Is it too late to expand?

Realtor · San Diego · Member since 2022 · 28 posts · 20 votes

Hello, I'm old and new to investing in Real Estate. I have been a Real Estate agent for almost 27 yrs (IL and CA). Along the way, I picked up a couple of investment properties admittedly (embarrassingly) without underwriting very well. Luckily, I did well on a flip in Northern California and have owned a condo and a townhome in Chicago IL (both LTRs) for a decade or so. Both are in great locations and I have no problems renting them with little to no vacancies and great tenants for the most part but it was unbearably slow to get here. We manage them ourselves (from afar) since we already have people we trust there. I'd like to add a small multifamily (2-4) to our portfolio next. We live in SoCal now and find it difficult to find anything here that pencils out. I have about 9 yrs left before retirement and am looking for advice and debating either a) getting another property in Chicago (cons: tenant-landlord ordinance & escalating property taxes, pros: existing relationships, market knowledge and my desire to visit friends and family there often) or alternate locations I'm considering > Kansas City, MO > Knoxville, TN > Peoria, IL > Winston Salem, NC. I've never been to any of these places. I'm looking for that unicorn with a mix of cash flow (6-8% cash on cash) and appreciation within the next 7-10 years, preferring a location with diverse industries/employment. I prefer B to A- locations. I've got some flexibility in pricing but the numbers need to work (or work within 12 months with a larger upside). I've been listening to Dion McNeeley lately and find him fascinating. I really like his desire to be as efficient as possible owning as few rentals as necessary. I'd love any input!

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Jonathan KlemmBusiness Member

Moderator

Contractor · Chicago, IL · Member since 2016 · 4k+ posts · 2k+ votes

8mo

It's never too late to expand @Lisa Peck!

You can still find that unicorn mix of appreciation and cashflow right here in Chicago! Some of our near suburbs in the west like Cicero, Berwyn, Oak Park, River Forest are great for those.

Also, some of the South East Chicago neighborhoods are for sure on the up and up still like Washington Park, Bronzeville, Woodlawn, etc.

If you have a solid team here I suggest digging deeper in to the market...I am, of course, biased and everything you said is true on taxes, tenant ordinances etc.

Happy to discuss more if you needs some boots on the ground input.

[email protected]

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Caleb Brown
Real Estate Agent · Kansas City · Member since 2018 · 4k+ posts · 3k+ votes
8mo
Happy to chat on KC. It's doable to find
1 Reply
- Lisa PeckPro Member
  OP
  Realtor · San Diego · Member since 2022 · 28 posts · 20 votes
  8mo
  Quote from @Caleb Brown:
  
  Happy to chat on KC. It's doable to find
  
  Appreciate you @Caleb. I will reach out if KC seems the way to go.
  1 Reply
Aaron ZimmermanBusiness Member
Accountant · Chicago, IL · Member since 2018 · 2k+ posts · 1k+ votes
8mo
It is Never too late to invest. To me, your odds of success increase with where your network is so I'd personally favor whereeever you've currently invested as you know those areas best.

If you bought out of state properties, you'd want to build your core 4 of real estate agent, property manager, contractor, and lender to get deals done. Easier said than done, but it is Doable.
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- Lisa PeckPro Member
  OP
  Realtor · San Diego · Member since 2022 · 28 posts · 20 votes
  8mo
  Quote from @Aaron Zimmerman:
  
  It is Never too late to invest. To me, your odds of success increase with where your network is so I'd personally favor whereeever you've currently invested as you know those areas best.
  
  If you bought out of state properties, you'd want to build your core 4 of real estate agent, property manager, contractor, and lender to get deals done. Easier said than done, but it is Doable.
  
  Thanks Aaron!
  0 Reply
Corby GoadeBusiness Member
Investor · Boise, ID · Member since 2014 · 3k+ posts · 3k+ votes
8mo
Short answer- it's NEVER too late, especially if you have kids to leave a legacy to.
However, chasing cash flow at the onset is a good way to go broke. Quality properties in growing areas. Sure, they won't perform great on year one, but over time, those properties will be much more passive and cash flow much better than C properties in the midwest.
3 Reply
- Lisa PeckPro Member
  OP
  Realtor · San Diego · Member since 2022 · 28 posts · 20 votes
  8mo
  Quote from @Corby Goade:
  
  Short answer- it's NEVER too late, especially if you have kids to leave a legacy to.
  However, chasing cash flow at the onset is a good way to go broke. Quality properties in growing areas. Sure, they won't perform great on year one, but over time, those properties will be much more passive and cash flow much better than C properties in the midwest.
  
  Thank you @Corby!
  1 Reply
Keith Mintz
Real Estate Agent · San Diego, CA · Member since 2023 · 189 posts · 88 votes
8mo
Quote from @Lisa Peck:

Hello, I'm old and new to investing in Real Estate. I have been a Real Estate agent for almost 27 yrs (IL and CA). Along the way, I picked up a couple of investment properties admittedly (embarrassingly) without underwriting very well. Luckily, I did well on a flip in Northern California and have owned a condo and a townhome in Chicago IL (both LTRs) for a decade or so. Both are in great locations and I have no problems renting them with little to no vacancies and great tenants for the most part but it was unbearably slow to get here. We manage them ourselves (from afar) since we already have people we trust there. I'd like to add a small multifamily (2-4) to our portfolio next. We live in SoCal now and find it difficult to find anything here that pencils out. I have about 9 yrs left before retirement and am looking for advice and debating either a) getting another property in Chicago (cons: tenant-landlord ordinance & escalating property taxes, pros: existing relationships, market knowledge and my desire to visit friends and family there often) or alternate locations I'm considering > Kansas City, MO > Knoxville, TN > Peoria, IL > Winston Salem, NC. I've never been to any of these places. I'm looking for that unicorn with a mix of cash flow (6-8% cash on cash) and appreciation within the next 7-10 years, preferring a location with diverse industries/employment. I prefer B to A- locations. I've got some flexibility in pricing but the numbers need to work (or work within 12 months with a larger upside). I've been listening to Dion McNeeley lately and find him fascinating. I really like his desire to be as efficient as possible owning as few rentals as necessary. I'd love any input!

Great post—and appreciate the honesty. A lot of long-time agents end up in a similar spot.

One thing I'd gently challenge is the idea that the "unicorn" has to come purely from market selection. I've found it's getting harder to consistently hit 6–8% CoC with a straight LTR approach, even in otherwise solid markets.

With small multifamily especially, I’ve personally seen strong results by focusing on operational upside rather than just rent growth—renting by the room, furnished housing, and in one case operating a property as a sober living home. All have materially outperformed traditional LTRs in similar locations.

That’s why markets you already know (like Chicago) can still make sense despite the friction—relationships and local knowledge matter a lot when you’re doing anything beyond vanilla rentals.

I also like Dion’s “fewer doors, higher efficiency” mindset. Strategies that increase income now create flexibility and let appreciation be the upside, not the requirement.

Aside from traditional LTRs, I suggest exploring creative operating strategies to get those higher returns.
3 Reply
- Lisa PeckPro Member
  OP
  Realtor · San Diego · Member since 2022 · 28 posts · 20 votes
  8mo
  Quote from @Keith Mintz:
  
  Quote from @Lisa Peck:
  
  Hello, I'm old and new to investing in Real Estate. I have been a Real Estate agent for almost 27 yrs (IL and CA). Along the way, I picked up a couple of investment properties admittedly (embarrassingly) without underwriting very well. Luckily, I did well on a flip in Northern California and have owned a condo and a townhome in Chicago IL (both LTRs) for a decade or so. Both are in great locations and I have no problems renting them with little to no vacancies and great tenants for the most part but it was unbearably slow to get here. We manage them ourselves (from afar) since we already have people we trust there. I'd like to add a small multifamily (2-4) to our portfolio next. We live in SoCal now and find it difficult to find anything here that pencils out. I have about 9 yrs left before retirement and am looking for advice and debating either a) getting another property in Chicago (cons: tenant-landlord ordinance & escalating property taxes, pros: existing relationships, market knowledge and my desire to visit friends and family there often) or alternate locations I'm considering > Kansas City, MO > Knoxville, TN > Peoria, IL > Winston Salem, NC. I've never been to any of these places. I'm looking for that unicorn with a mix of cash flow (6-8% cash on cash) and appreciation within the next 7-10 years, preferring a location with diverse industries/employment. I prefer B to A- locations. I've got some flexibility in pricing but the numbers need to work (or work within 12 months with a larger upside). I've been listening to Dion McNeeley lately and find him fascinating. I really like his desire to be as efficient as possible owning as few rentals as necessary. I'd love any input!
  
  Great post—and appreciate the honesty. A lot of long-time agents end up in a similar spot.
  
  One thing I'd gently challenge is the idea that the "unicorn" has to come purely from market selection. I've found it's getting harder to consistently hit 6–8% CoC with a straight LTR approach, even in otherwise solid markets.
  
  With small multifamily especially, I’ve personally seen strong results by focusing on operational upside rather than just rent growth—renting by the room, furnished housing, and in one case operating a property as a sober living home. All have materially outperformed traditional LTRs in similar locations.
  
  That’s why markets you already know (like Chicago) can still make sense despite the friction—relationships and local knowledge matter a lot when you’re doing anything beyond vanilla rentals.
  
  I also like Dion’s “fewer doors, higher efficiency” mindset. Strategies that increase income now create flexibility and let appreciation be the upside, not the requirement.
  
  Aside from traditional LTRs, I suggest exploring creative operating strategies to get those higher returns.
  
  Thanks for the input Keith, I agree and left out the part about having a plan for the first 12-18 months to get to that CoC. I look forward to learning from folks like yourself about how to get this. Once again, something missing from my LTRs (not from the flip tho:). The piece I look to learn from is the market selection. I value what I have built so far but unsure if the ROI (on $$, energy, time) is the highest and best use me as I look to expand. I just need to find the right deals in Chicago! If not right here nearby to San Diego. Starting a whole new market is probably best suited for me 10 years ago. Thanks for your input. Love to connect offline, I'll ping you.
  0 Reply
Kerlous TadresBusiness Member
Realtor · Columbus, OH · Member since 2023 · 1k+ posts · 1k+ votes
8mo
@Lisa Peck, I’d pick a place with diverse jobs, landlord-friendly rules, and a strong 2–4 unit rental pool, then buy near major employers where you can raise rents or cut expenses within 12 months. If your current area is tempting, I’d only do it if it still hits your 6–8% cash-on-cash after you stress-test property taxes and tenant regulations.

[email protected]614-490-1163
Kerlous Tadres | Reafco Real Estate540 Reviews
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- Lisa PeckPro Member
  OP
  Realtor · San Diego · Member since 2022 · 28 posts · 20 votes
  8mo
  Quote from @Kerlous Tadres:
  
  @Lisa Peck, I’d pick a place with diverse jobs, landlord-friendly rules, and a strong 2–4 unit rental pool, then buy near major employers where you can raise rents or cut expenses within 12 months. If your current area is tempting, I’d only do it if it still hits your 6–8% cash-on-cash after you stress-test property taxes and tenant regulations.
  
  Thank you Kerlous! Appreciate the input.
  1 Reply
Jonathan KlemmBusiness Member
Moderator
Contractor · Chicago, IL · Member since 2016 · 4k+ posts · 2k+ votes
8mo
It's never too late to expand @Lisa Peck!
You can still find that unicorn mix of appreciation and cashflow right here in Chicago! Some of our near suburbs in the west like Cicero, Berwyn, Oak Park, River Forest are great for those.
Also, some of the South East Chicago neighborhoods are for sure on the up and up still like Washington Park, Bronzeville, Woodlawn, etc.
If you have a solid team here I suggest digging deeper in to the market...I am, of course, biased and everything you said is true on taxes, tenant ordinances etc.
Happy to discuss more if you needs some boots on the ground input.
[email protected]
Quality Builders4.966 Reviews
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5 Reply
- Lisa PeckPro Member
  OP
  Realtor · San Diego · Member since 2022 · 28 posts · 20 votes
  8mo
  Quote from @Jonathan Klemm:
  
  It's never too late to expand @Lisa Peck!
  You can still find that unicorn mix of appreciation and cashflow right here in Chicago! Some of our near suburbs in the west like Cicero, Berwyn, Oak Park, River Forest are great for those.
  Also, some of the South East Chicago neighborhoods are for sure on the up and up still like Washington Park, Bronzeville, Woodlawn, etc.
  If you have a solid team here I suggest digging deeper in to the market...I am, of course, biased and everything you said is true on taxes, tenant ordinances etc.
  Happy to discuss more if you needs some boots on the ground input.
  
  Thank you Jonathan, love this! I'd love to connect and will ping you.
  1 Reply
Kenneth GarrettPro Member
Investor · Florida Panhandle/Illinois · Member since 2016 · 4k+ posts · 3k+ votes
8mo
@Lisa Peck
Like others have said it’s never to late. I know a couple in their upper 70’s who add a property once a year.
You might like to try the suburbs outside of the Chicago limits. Not so many rules and difficulties working with the city. Of course, you need to do your due diligence with any area you invest in.
I have properties in the suburbs outside of Chicago and in Florida and Georgia. Having a team in each area is critical. Once that is established you can invest anywhere that makes sense.
I have never invested in Chicago. They are just not landlord friendly. That’s not to say you can’t or shouldn’t invest there. Many investors do and have found a way to navigate the city.
Best of Luck!
1 Reply
- Lisa PeckPro Member
  OP
  Realtor · San Diego · Member since 2022 · 28 posts · 20 votes
  8mo
  Quote from @Kenneth Garrett:
  
  @Lisa Peck
  Like others have said it’s never to late. I know a couple in their upper 70’s who add a property once a year.
  You might like to try the suburbs outside of the Chicago limits. Not so many rules and difficulties working with the city. Of course, you need to do your due diligence with any area you invest in.
  I have properties in the suburbs outside of Chicago and in Florida and Georgia. Having a team in each area is critical. Once that is established you can invest anywhere that makes sense.
  I have never invested in Chicago. They are just not landlord friendly. That’s not to say you can’t or shouldn’t invest there. Many investors do and have found a way to navigate the city.
  Best of Luck!
  
  Thanks for the honest input. I appreciate and respect your input! I'm not opposed to suburbs at all! I like how Dion McNeeley mentions the "not great schools" areas to focus on (avoiding the high tax bill and high turnover associated with this). Not sure which suburbs these are though since I used to focus on great schools.
  0 Reply
Pierre Guirguis
Lender · Marlboro, NJ · Member since 2025 · 243 posts · 150 votes
8mo
Not too late at all but the framing matters.

With a 7–10 year horizon, the goal isn’t finding a unicorn. It’s avoiding markets where the downside is asymmetric. A clean 2–4 unit in a B/B+ area with durable employment and boring cash flow will quietly outperform something “sexier” that relies on rent growth or appreciation doing the heavy lifting.

The Chicago question is really about tradeoffs, not right or wrong. Familiarity, trusted boots on the ground, and existing infrastructure matter more than people admit, especially when you’re managing from afar. The ordinance and tax risks are real, but they’re at least known risks.

In the other markets you mentioned, I’d be less worried about never having visited and more focused on underwriting discipline and management quality. If a deal needs perfect execution to hit 6–8% cash-on-cash, it’s probably the wrong deal for this stage. The ones that work tend to have a little operational slack and still pencil conservatively.

Efficiency matters more than scale here. Fewer properties that actually perform beats chasing growth late in the cycle.
1 Reply
- Lisa PeckPro Member
  OP
  Realtor · San Diego · Member since 2022 · 28 posts · 20 votes
  8mo
  Quote from @Pierre Guirguis:
  
  Not too late at all but the framing matters.
  
  With a 7–10 year horizon, the goal isn’t finding a unicorn. It’s avoiding markets where the downside is asymmetric. A clean 2–4 unit in a B/B+ area with durable employment and boring cash flow will quietly outperform something “sexier” that relies on rent growth or appreciation doing the heavy lifting.
  
  The Chicago question is really about tradeoffs, not right or wrong. Familiarity, trusted boots on the ground, and existing infrastructure matter more than people admit, especially when you’re managing from afar. The ordinance and tax risks are real, but they’re at least known risks.
  
  In the other markets you mentioned, I’d be less worried about never having visited and more focused on underwriting discipline and management quality. If a deal needs perfect execution to hit 6–8% cash-on-cash, it’s probably the wrong deal for this stage. The ones that work tend to have a little operational slack and still pencil conservatively.
  
  Efficiency matters more than scale here. Fewer properties that actually perform beats chasing growth late in the cycle.
  
  Thanks, at this age, I'm only looking of sexy Numbers! Quiet and boring is quite sexy!
  1 Reply
Claire Shi
Member since 2026 · 4 posts · 4 votes
8mo
Hi Lisa, I’m also new to BP. I’m actually interested in investing in Chicago, but I’m only considering LTRs. Do you know how the return rates look there? Where I am near the DC area, properties are expensive and it’s tough to get good cash flow, so I’m exploring other markets.
1 Reply
- Lisa PeckPro Member
  OP
  Realtor · San Diego · Member since 2022 · 28 posts · 20 votes
  8mo
  Quote from @Claire Shi:
  
  Hi Lisa, I’m also new to BP. I’m actually interested in investing in Chicago, but I’m only considering LTRs. Do you know how the return rates look there? Where I am near the DC area, properties are expensive and it’s tough to get good cash flow, so I’m exploring other markets.
  
  Hi there @Claire Shi welcome to BP. I've lurked for years and excited to activate. I had a lot of investor clients when I sold Real Estate there. All of them were in the market because they either knew the market or had some tie there (relatives/ future retirement / accidental investors who owned and then moved etc). The city has strict tenant landlord ordinance that strongly favor the tenant, some that now landlord could ever win. The appreciation is lackluster at best and there is more demand there now than I've seen in the last 30 years. So, if you want to be in Chicago, build your team and analyze your numbers well (wish I did this earlier). I'll be checking numbers on dead in the suburbs and the south side. I'm currently holding property on the north side. Happy to connect if you ever want to discuss them details/numbers.
  1 Reply
Jimmy LieuBusiness Member
Real Estate Agent · Columbus, OH · Member since 2019 · 3k+ posts · 2k+ votes
8mo
Quote from @Lisa Peck:

Hello, I'm old and new to investing in Real Estate. I have been a Real Estate agent for almost 27 yrs (IL and CA). Along the way, I picked up a couple of investment properties admittedly (embarrassingly) without underwriting very well. Luckily, I did well on a flip in Northern California and have owned a condo and a townhome in Chicago IL (both LTRs) for a decade or so. Both are in great locations and I have no problems renting them with little to no vacancies and great tenants for the most part but it was unbearably slow to get here. We manage them ourselves (from afar) since we already have people we trust there. I'd like to add a small multifamily (2-4) to our portfolio next. We live in SoCal now and find it difficult to find anything here that pencils out. I have about 9 yrs left before retirement and am looking for advice and debating either a) getting another property in Chicago (cons: tenant-landlord ordinance & escalating property taxes, pros: existing relationships, market knowledge and my desire to visit friends and family there often) or alternate locations I'm considering > Kansas City, MO > Knoxville, TN > Peoria, IL > Winston Salem, NC. I've never been to any of these places. I'm looking for that unicorn with a mix of cash flow (6-8% cash on cash) and appreciation within the next 7-10 years, preferring a location with diverse industries/employment. I prefer B to A- locations. I've got some flexibility in pricing but the numbers need to work (or work within 12 months with a larger upside). I've been listening to Dion McNeeley lately and find him fascinating. I really like his desire to be as efficient as possible owning as few rentals as necessary. I'd love any input!
Hi Lisa, welcome to BP! It sounds like you’ve built a strong foundation with your past rentals and your experience as an agent gives you a huge advantage in analyzing deals, even if some early ones didn’t pencil perfectly. Since you’re looking for that mix of cash flow and appreciation, and you like the idea of owning fewer, efficient rentals, I’d suggest taking a hard look at Columbus, Ohio. I moved from Portland to Columbus in 2020 to start investing and now own 10+ rentals, and the market here is still incredibly strong. You can find 2–4 unit properties in good B to B- neighborhoods that hit the 1% rule and cash flow right away, plus the macroeconomics are on fire with tons of population growth, job growth, and companies like Intel, Amazon, Google, Facebook, Honda, Microsoft, LG, and Anduril expanding here. The long-term appreciation potential is real, and you don’t have to deal with the same super-high taxes or tenant-landlord headaches you’d get in Chicago or SoCal. For a first or next multifamily, Columbus lets you combine steady cash flow with growth upside, and with the right local team, managing from out-of-state is very doable. Happy to connect and answer any questions you have!

[email protected]614-300-7535
Jimmy Lieu, Red 1 Realty4.9120 Reviews
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Lisa PeckPro Member
OP
Realtor · San Diego · Member since 2022 · 28 posts · 20 votes
8mo
Thanks Jimmy, I'll take a look at a Columbus, OH!
0 Reply
Dan H.Pro Member
Investor · Poway, CA · Member since 2015 · 7k+ posts · 8k+ votes
8mo
First you do not look old in your picture.
Second all markets have challenges. I highly recommend you stay in a market you are knowledgeable whether that is Chicago or San Diego over a market you have not visited.
I know very little about the Chicago market and highly suspect you know more than I do about that market.
San Diego has a lot of challenges. Seems you already know to perform thorough and conservative underwriting. My belief is if you do this, mls purchases with high LTV market financing will reflect negative cash flow. However, you are a realtor in San Diego. Look for off market RE opportunities or alternative financing. Consider alternative rent models.
Recognize the number one thing that dictates cash flow over a long hold is market rent growth and it is a very rare market that has historically had better market rent growth than San Diego.
My last San Diego purchase was one of the most cash flow negative I ever heard about per unit. $2.25m quad purchase, $6k/month total rents. That off market price reflected a discount due to the various challenges including the pathetic rents. Today it is worth ~$3.5m and has rent that I hope exceeds $25k/month for 2026. I show this not to brag (that is a side benefit, lol), but to show you what is possible.
With your realtor connections, you should be able to find local properties that forecast a good ROI.
I think you have advantages in the San Diego market that exceeds many local investors and that you should consider using those advantages.

good luck
2 Reply
- Lisa PeckPro Member
  OP
  Realtor · San Diego · Member since 2022 · 28 posts · 20 votes
  8mo
  Quote from @Dan H.:
  
  First you do not look old in your picture.
  Second all markets have challenges. I highly recommend you stay in a market you are knowledgeable whether that is Chicago or San Diego over a market you have not visited.
  I know very little about the Chicago market and highly suspect you know more than I do about that market.
  San Diego has a lot of challenges. Seems you already know to perform thorough and conservative underwriting. My belief is if you do this, mls purchases with high LTV market financing will reflect negative cash flow. However, you are a realtor in San Diego. Look for off market RE opportunities or alternative financing. Consider alternative rent models.
  Recognize the number one thing that dictates cash flow over a long hold is market rent growth and it is a very rare market that has historically had better market rent growth than San Diego.
  My last San Diego purchase was one of the most cash flow negative I ever heard about per unit. $2.25m quad purchase, $6k/month total rents. That off market price reflected a discount due to the various challenges including the pathetic rents. Today it is worth ~$3.5m and has rent that I hope exceeds $25k/month for 2026. I show this not to brag (that is a side benefit, lol), but to show you what is possible.
  With your realtor connections, you should be able to find local properties that forecast a good ROI.
  I think you have advantages in the San Diego market that exceeds many local investors and that you should consider using those advantages.
  
  good luck
  
  Thanks Dan, I should mention that I'm new(ish) to the area so Im not entrenched like I was in other markets. Love to hear more about your purchases here. What was the time horizon on that SD quad?
  
  0 Reply
- Dan H.Pro Member
  Investor · Poway, CA · Member since 2015 · 7k+ posts · 8k+ votes
  8mo
  Quote from @Lisa Peck:
  
  Quote from @Dan H.:
  
  First you do not look old in your picture.
  Second all markets have challenges. I highly recommend you stay in a market you are knowledgeable whether that is Chicago or San Diego over a market you have not visited.
  I know very little about the Chicago market and highly suspect you know more than I do about that market.
  San Diego has a lot of challenges. Seems you already know to perform thorough and conservative underwriting. My belief is if you do this, mls purchases with high LTV market financing will reflect negative cash flow. However, you are a realtor in San Diego. Look for off market RE opportunities or alternative financing. Consider alternative rent models.
  Recognize the number one thing that dictates cash flow over a long hold is market rent growth and it is a very rare market that has historically had better market rent growth than San Diego.
  My last San Diego purchase was one of the most cash flow negative I ever heard about per unit. $2.25m quad purchase, $6k/month total rents. That off market price reflected a discount due to the various challenges including the pathetic rents. Today it is worth ~$3.5m and has rent that I hope exceeds $25k/month for 2026. I show this not to brag (that is a side benefit, lol), but to show you what is possible.
  With your realtor connections, you should be able to find local properties that forecast a good ROI.
  I think you have advantages in the San Diego market that exceeds many local investors and that you should consider using those advantages.
  
  good luck
  
  Thanks Dan, I should mention that I'm new(ish) to the area so Im not entrenched like I was in other markets. Love to hear more about your purchases here. What was the time horizon on that SD quad?
  
  Purchased Dec 2021, stabilized early 2025. We purchased at a discount because of condition and current rent. Bugged me that city assigned a $250k higher valuation for property tax because they viewed the value higher. There was no comp with that low a rent point or even close to that low a rent point. How do you value a property that has one unit paying nothing and 3 units paying half of market rent? My view is it should be the price the buyer and seller agree on. The rent point was a challenge because the outside had issues but 3 of the 4 units were not so thrashed to warrant a full rehab to qualify for the ab1482 rehab requirement. I initially was thinking brrrr but the interest rates rose enough that I switched to only the value add. So we did one unit at a time and only ended up terminating the lease on the one that needed the extensive rehab. That tenant had told us a planned move out but chose not to so we had to go through the ab1482/San Diego rent stabilization process to do a no fault eviction and the tenant not moving when he indicated ended up costing us 2 months rent paid to tenant. But he was a good tenant (but paying about half of market rent) so I do not believe he intentionally lied to get the 2 months rent but end result was the same as if he intentionally lied. So it was a slightly slow stabilization. Rent control challenges combined with no longer planning a brrrr resulted in it taking 3 years.
  
  In late 2024 (after returning from BOCon), I had invited a full dump on this acquisition on this site (BP). I was going to show the value add, the financials, and answer any/all questions. A decent amount of people have xpressed interest in coming. Only one showed up and she showed up outside the scheduled time window. Because I was still at the property I would have gone over financials, value add, any thing. But she only had enough time to look at things.
  
  I would like to think if given the same opportunity when young, and would have jumped at the opportunity but I had a friend whose mom owned a few apartment buildings. I never asked her about anything related to RE even though they were crushing it. Today that family has very large RE holdings virtually completely under the radar. Who knows how much this could have accelerated my RE success.
  
  Good luck
  
  2 Reply
Arman AhmedPro Member
Real Estate Agent · Columbus Cleveland Dayton, OH · Member since 2024 · 2k+ posts · 938 votes
8mo
@Lisa Peck
It’s definitely not too late. With your background and clear goals, you’re actually in a great position to be picky. A lot of investors chasing real cash flow and long-term appreciation are quietly moving toward Midwest markets where B to A- neighborhoods still pencil, entry prices make sense, and diverse employment supports stable demand. Small multifamily there aligns really well with the “fewer, better assets” mindset you mentioned. Happy to share what I’m seeing if you want to compare notes.

[email protected]614-418-6081
1 Reply
- Lisa PeckPro Member
  OP
  Realtor · San Diego · Member since 2022 · 28 posts · 20 votes
  8mo
  Quote from @Arman Ahmed:
  
  @Lisa Peck
  It’s definitely not too late. With your background and clear goals, you’re actually in a great position to be picky. A lot of investors chasing real cash flow and long-term appreciation are quietly moving toward Midwest markets where B to A- neighborhoods still pencil, entry prices make sense, and diverse employment supports stable demand. Small multifamily there aligns really well with the “fewer, better assets” mindset you mentioned. Happy to share what I’m seeing if you want to compare notes.
  
  Thank you very much Arman! I'll take a look at Columbus OH, I appreciate your input.
  0 Reply
- Lisa PeckPro Member
  OP
  Realtor · San Diego · Member since 2022 · 28 posts · 20 votes
  8mo
  Quote from @Arman Ahmed:
  
  @Lisa Peck
  It’s definitely not too late. With your background and clear goals, you’re actually in a great position to be picky. A lot of investors chasing real cash flow and long-term appreciation are quietly moving toward Midwest markets where B to A- neighborhoods still pencil, entry prices make sense, and diverse employment supports stable demand. Small multifamily there aligns really well with the “fewer, better assets” mindset you mentioned. Happy to share what I’m seeing if you want to compare notes.
  
  Thank you very much Arman! I'll take a look at Columbus OH, I appreciate your input.
  0 Reply
Alfath AhmedBusiness Member
Real Estate Agent · Columbus, OH · Member since 2022 · 1k+ posts · 1k+ votes
8mo
Quote from @Lisa Peck:

Hello, I'm old and new to investing in Real Estate. I have been a Real Estate agent for almost 27 yrs (IL and CA). Along the way, I picked up a couple of investment properties admittedly (embarrassingly) without underwriting very well. Luckily, I did well on a flip in Northern California and have owned a condo and a townhome in Chicago IL (both LTRs) for a decade or so. Both are in great locations and I have no problems renting them with little to no vacancies and great tenants for the most part but it was unbearably slow to get here. We manage them ourselves (from afar) since we already have people we trust there. I'd like to add a small multifamily (2-4) to our portfolio next. We live in SoCal now and find it difficult to find anything here that pencils out. I have about 9 yrs left before retirement and am looking for advice and debating either a) getting another property in Chicago (cons: tenant-landlord ordinance & escalating property taxes, pros: existing relationships, market knowledge and my desire to visit friends and family there often) or alternate locations I'm considering > Kansas City, MO > Knoxville, TN > Peoria, IL > Winston Salem, NC. I've never been to any of these places. I'm looking for that unicorn with a mix of cash flow (6-8% cash on cash) and appreciation within the next 7-10 years, preferring a location with diverse industries/employment. I prefer B to A- locations. I've got some flexibility in pricing but the numbers need to work (or work within 12 months with a larger upside). I've been listening to Dion McNeeley lately and find him fascinating. I really like his desire to be as efficient as possible owning as few rentals as necessary. I'd love any input!

Good work on investing Lisa. You can find income driven growth in the midwest pretty easily. It is hard to invest in the west-coast because your money doesn't go very far and it is a tenant-friendly market.

I work with a ton of Californians and they like buying 2-4 units and larger asset classes due to cashflow and you can raise the cap rates very easily through simple improvements.
You should look into the Ohio Market for large multi-family. Columbus is great for equity plays and appreciation. Cleveland is great for cashflow. Dayton is more about affordability and stability.

I've sold over 120+ deals this past year and own 28+ rental units here in Columbus. Happy to share my resources and lender/PM contacts.

Let me know if you want to hop on a call to discuss strategy.
[email protected]614-802-5698
ReafCo | Ahmed Group 536 Reviews
Website View Page
2 Reply
- Lisa PeckPro Member
  OP
  Realtor · San Diego · Member since 2022 · 28 posts · 20 votes
  8mo
  Quote from @Alfath Ahmed:
  
  Quote from @Lisa Peck:
  
  Hello, I'm old and new to investing in Real Estate. I have been a Real Estate agent for almost 27 yrs (IL and CA). Along the way, I picked up a couple of investment properties admittedly (embarrassingly) without underwriting very well. Luckily, I did well on a flip in Northern California and have owned a condo and a townhome in Chicago IL (both LTRs) for a decade or so. Both are in great locations and I have no problems renting them with little to no vacancies and great tenants for the most part but it was unbearably slow to get here. We manage them ourselves (from afar) since we already have people we trust there. I'd like to add a small multifamily (2-4) to our portfolio next. We live in SoCal now and find it difficult to find anything here that pencils out. I have about 9 yrs left before retirement and am looking for advice and debating either a) getting another property in Chicago (cons: tenant-landlord ordinance & escalating property taxes, pros: existing relationships, market knowledge and my desire to visit friends and family there often) or alternate locations I'm considering > Kansas City, MO > Knoxville, TN > Peoria, IL > Winston Salem, NC. I've never been to any of these places. I'm looking for that unicorn with a mix of cash flow (6-8% cash on cash) and appreciation within the next 7-10 years, preferring a location with diverse industries/employment. I prefer B to A- locations. I've got some flexibility in pricing but the numbers need to work (or work within 12 months with a larger upside). I've been listening to Dion McNeeley lately and find him fascinating. I really like his desire to be as efficient as possible owning as few rentals as necessary. I'd love any input!
  
  Good work on investing Lisa. You can find income driven growth in the midwest pretty easily. It is hard to invest in the west-coast because your money doesn't go very far and it is a tenant-friendly market.
  
  I work with a ton of Californians and they like buying 2-4 units and larger asset classes due to cashflow and you can raise the cap rates very easily through simple improvements.
  You should look into the Ohio Market for large multi-family. Columbus is great for equity plays and appreciation. Cleveland is great for cashflow. Dayton is more about affordability and stability.
  
  I've sold over 120+ deals this past year and own 28+ rental units here in Columbus. Happy to share my resources and lender/PM contacts.
  
  Let me know if you want to hop on a call to discuss strategy.
  
  Thank you Alfaro, Columbus does sound interesting. I'll add it to the list for sure. Appreciate you!
  0 Reply
Terrance HillPro Member
Realtor · Memphis, TN · Member since 2010 · 425 posts · 117 votes
8mo
Hi Lisa,
Not too late at all—you’re well positioned.

Your edge is experience + existing assets. With a 7–10 year window, focus on one strong 2–4 unit over scaling.
- Chicago = best execution risk due to relationships, despite taxes.
- KC / Knoxville / Winston-Salem = solid B/B- markets, but team-building is key.
- Peoria = cash flow first, appreciation is deal-specific.
Your 6–8% CoC + appreciation goal is realistic with light value-add small multifamily and tight management (very Dion-style).
1 Reply
- Lisa PeckPro Member
  OP
  Realtor · San Diego · Member since 2022 · 28 posts · 20 votes
  8mo
  Quote from @Terrance Hill:
  
  Hi Lisa,
  Not too late at all—you’re well positioned.
  
  Your edge is experience + existing assets. With a 7–10 year window, focus on one strong 2–4 unit over scaling.
  
  Chicago = best execution risk due to relationships, despite taxes.
  KC / Knoxville / Winston-Salem = solid B/B- markets, but team-building is key.
  Peoria = cash flow first, appreciation is deal-specific.
  
  Your 6–8% CoC + appreciation goal is realistic with light value-add small multifamily and tight management (very Dion-style).
  
  Thank you for the solid feedback!
  0 Reply
Bo SmithPro Member
Hinton, WV · Member since 2026 · 1k+ posts · 373 votes
8mo
Your agent background is huge - you can spot neighborhood shifts before most investors notice. Since you're eyeing unfamiliar markets, maybe factor in your "oh crap" response time if something goes sideways. Still leaning Chicago or ready to dive into new territory?
1 Reply
- Lisa PeckPro Member
  OP
  Realtor · San Diego · Member since 2022 · 28 posts · 20 votes
  8mo
  Quote from @Bo Smith:
  
  Your agent background is huge - you can spot neighborhood shifts before most investors notice. Since you're eyeing unfamiliar markets, maybe factor in your "oh crap" response time if something goes sideways. Still leaning Chicago or ready to dive into new territory?
  
  Yes, thanks Bo, Chicago will be a great starting spot.
  0 Reply
Bernice RetzloffPro Member
Memphis, TN · Member since 2024 · 234 posts · 100 votes
8mo
Hey @Lisa Peck! First off, respect for the self-awareness. A lot of very successful investors only admit after the fact that early deals weren’t underwritten well… you just said it out loud, And honestly, owning clean LTRs for a decade with low vacancy and good tenants is still a win, even if it felt slow.

A few thoughts based on where you’re at:

Chicago vs a new market

Your pros/cons list for Chicago is spot on. The big hidden cost there isn’t finding tenants — it’s:

Tenant-landlord ordinances getting tighter

Property taxes eroding returns year after year

Cash flow being capped unless you add value

If your goal were “low friction + familiarity,” Chicago makes sense. But if the goal is adding a 2–4 unit that actually moves the needle before retirement, I’d be cautious about putting more capital there unless the deal has a very clear value-add angle.

The markets you listed

You’re thinking in the right direction by prioritizing:

Diverse employment

B / A- neighborhoods

Modest but real cash flow plus appreciation

Quick high-level take:

Kansas City – Solid fundamentals, competitive right now, still workable but tighter margins

Knoxville – Strong appreciation story, harder to find true cash flow unless you’re early or adding value

Peoria – Cash flow exists, but appreciation and liquidity are more limited

Winston-Salem – Underrated, decent balance, but neighborhood selection matters a lot

None of these are “wrong,” but each requires boots-on-the-ground intel to avoid buying something that looks good on paper and underperforms in reality.

About the unicorn (6–8% CoC + appreciation)

That is still achievable, but usually with one or more of these:

Smaller multifamily (2–4 units vs larger)

Light to moderate value-add within 6–12 months

Investor-friendly management keeping expenses tight

Buying slightly under market (not retail MLS deals)

It’s less about where and more about how the deal is sourced and operated.

I’m a real estate agent based in Memphis, TN, and I work primarily with out-of-state investors looking for exactly what you’re describing. Efficient portfolios, not dozens of doors just to feel busy. We also work closely with FoundationPM.com, so underwriting, operations, and long-term performance are front and center from day one.

Memphis tends to check a lot of your boxes:

True B-class neighborhoods with liquidity

2–4 units that can hit your CoC targets

Diverse employment base (logistics, healthcare, education, government)

Still enough spread for value-add without relying on wild assumptions

It’s not flashy, but it’s efficient. Which lines up well with the Dion McNeeley philosophy you mentioned.

If you’re open to it, I’d suggest:

Comparing one Chicago deal vs one new-market deal side by side

Underwriting both with the same conservative assumptions

Letting the math (and stress level) make the decision for you

Happy to connect if Memphis ever moves onto your shortlist or if you just want a sanity check on assumptions. You’re asking the right questions at exactly the right point in the journey.
901-664-1949
2 Reply
- Lisa PeckPro Member
  OP
  Realtor · San Diego · Member since 2022 · 28 posts · 20 votes
  8mo
  Quote from @Bernice Retzloff:
  
  Hey @Lisa Peck! First off, respect for the self-awareness. A lot of very successful investors only admit after the fact that early deals weren’t underwritten well… you just said it out loud, And honestly, owning clean LTRs for a decade with low vacancy and good tenants is still a win, even if it felt slow.
  
  A few thoughts based on where you’re at:
  
  Chicago vs a new market
  
  Your pros/cons list for Chicago is spot on. The big hidden cost there isn’t finding tenants — it’s:
  
  Tenant-landlord ordinances getting tighter
  
  Property taxes eroding returns year after year
  
  Cash flow being capped unless you add value
  
  If your goal were “low friction + familiarity,” Chicago makes sense. But if the goal is adding a 2–4 unit that actually moves the needle before retirement, I’d be cautious about putting more capital there unless the deal has a very clear value-add angle.
  
  The markets you listed
  
  You’re thinking in the right direction by prioritizing:
  
  Diverse employment
  
  B / A- neighborhoods
  
  Modest but real cash flow plus appreciation
  
  Quick high-level take:
  
  Kansas City – Solid fundamentals, competitive right now, still workable but tighter margins
  
  Knoxville – Strong appreciation story, harder to find true cash flow unless you’re early or adding value
  
  Peoria – Cash flow exists, but appreciation and liquidity are more limited
  
  Winston-Salem – Underrated, decent balance, but neighborhood selection matters a lot
  
  None of these are “wrong,” but each requires boots-on-the-ground intel to avoid buying something that looks good on paper and underperforms in reality.
  
  About the unicorn (6–8% CoC + appreciation)
  
  That is still achievable, but usually with one or more of these:
  
  Smaller multifamily (2–4 units vs larger)
  
  Light to moderate value-add within 6–12 months
  
  Investor-friendly management keeping expenses tight
  
  Buying slightly under market (not retail MLS deals)
  
  It’s less about where and more about how the deal is sourced and operated.
  
  I’m a real estate agent based in Memphis, TN, and I work primarily with out-of-state investors looking for exactly what you’re describing. Efficient portfolios, not dozens of doors just to feel busy. We also work closely with FoundationPM.com, so underwriting, operations, and long-term performance are front and center from day one.
  
  Memphis tends to check a lot of your boxes:
  
  True B-class neighborhoods with liquidity
  
  2–4 units that can hit your CoC targets
  
  Diverse employment base (logistics, healthcare, education, government)
  
  Still enough spread for value-add without relying on wild assumptions
  
  It’s not flashy, but it’s efficient. Which lines up well with the Dion McNeeley philosophy you mentioned.
  
  If you’re open to it, I’d suggest:
  
  Comparing one Chicago deal vs one new-market deal side by side
  
  Underwriting both with the same conservative assumptions
  
  Letting the math (and stress level) make the decision for you
  
  Happy to connect if Memphis ever moves onto your shortlist or if you just want a sanity check on assumptions. You’re asking the right questions at exactly the right point in the journey.
  
  Wow Bernice, thanks for the well presented and thorough out loud thinking, I really an appreciate it. YOu're are dead on with where I'm heading now. Let's stay connected, I hope to help you one day soon!
  0 Reply
Marc RiceBusiness Member
Real Estate Agent · Columbus Cleveland Dayton, OH · Member since 2018 · 2k+ posts · 1k+ votes
8mo
Quote from @Lisa Peck:

Hello, I'm old and new to investing in Real Estate. I have been a Real Estate agent for almost 27 yrs (IL and CA). Along the way, I picked up a couple of investment properties admittedly (embarrassingly) without underwriting very well. Luckily, I did well on a flip in Northern California and have owned a condo and a townhome in Chicago IL (both LTRs) for a decade or so. Both are in great locations and I have no problems renting them with little to no vacancies and great tenants for the most part but it was unbearably slow to get here. We manage them ourselves (from afar) since we already have people we trust there. I'd like to add a small multifamily (2-4) to our portfolio next. We live in SoCal now and find it difficult to find anything here that pencils out. I have about 9 yrs left before retirement and am looking for advice and debating either a) getting another property in Chicago (cons: tenant-landlord ordinance & escalating property taxes, pros: existing relationships, market knowledge and my desire to visit friends and family there often) or alternate locations I'm considering > Kansas City, MO > Knoxville, TN > Peoria, IL > Winston Salem, NC. I've never been to any of these places. I'm looking for that unicorn with a mix of cash flow (6-8% cash on cash) and appreciation within the next 7-10 years, preferring a location with diverse industries/employment. I prefer B to A- locations. I've got some flexibility in pricing but the numbers need to work (or work within 12 months with a larger upside). I've been listening to Dion McNeeley lately and find him fascinating. I really like his desire to be as efficient as possible owning as few rentals as necessary. I'd love any input!
Looks like you have done all the hard work and now just need to choose a market with a stable cash flow and appreciation.
[email protected]614-363-2787
Marc Rice | Investor Friendly Agent at Reafco Tailwind Team574 Reviews
Website View Page
1 Reply
James WachobBusiness Member
Real Estate Broker · Memphis, TN · Member since 2015 · 1k+ posts · 890 votes
8mo
Hey @Lisa Peck, really enjoyed reading your journey! I can totally relate to learning the hard way—sometimes you just have to dive in to figure things out. I’ve been helping investors in Memphis for over 20 years build rental portfolios, and one thing I’ve learned is that finding that mix of cash flow and long-term appreciation is all about the neighborhood and the numbers.

If you ever consider Memphis, it’s a market where you can hit that 6–8% cash-on-cash return, especially in solid B to A- areas. There’s also good employment diversity, and the city is very “street by street”—one street can be amazing, and three streets over can be a totally different story, so picking the right location is key. For investors like you who want to be efficient with just a few properties, Memphis really lets you do that without having to manage a dozen rentals.

It sounds like you’ve got a smart approach and a clear plan, and if you ever want to bounce ideas about Memphis neighborhoods and how to get strong numbers, happy to share what’s been working for investors here.
2 Reply
Lisa PeckPro Member
OP
Realtor · San Diego · Member since 2022 · 28 posts · 20 votes
8mo
@Marc Rice Thanks for the vote of confidence!
0 Reply
Lisa PeckPro Member
OP
Realtor · San Diego · Member since 2022 · 28 posts · 20 votes
8mo
@James Wachob thanks for the solid feedback!
0 Reply
Lee Burns
Investor · Chicago, IL · Member since 2018 · 315 posts · 149 votes
8mo
I think Henry Ford answers your question about being too late to expand in his quote "Whether you believe you can or you can't, you're right."
1 Reply
- Lisa PeckPro Member
  OP
  Realtor · San Diego · Member since 2022 · 28 posts · 20 votes
  7mo
  Quote from @Lee Burns:
  
  I think Henry Ford answers your question about being too late to expand in his quote "Whether you believe you can or you can't, you're right."
  
  Voila!!!
  0 Reply
Mendell GosnellBusiness Member
Property Manager · Salem, OR · Member since 2014 · 10 posts · 5 votes
7mo
The sooner the better, but never too late. I invest in Oregon and about 5 years ago started investing in AZ. I think the adage, "live where you want and invest where it makes sense" is some good advice. As you probably know, the first couple years tend to be low cash flow on most deals but over time Real Estate has a great track record. Always depends on your goals. However, real estate provides a lot of options. I am biased of course, but for those who have the aptitude for investing in real estate it is hard to beat.
All the best,
-Mendell
503-588-0940
Centurion Real Estate Management, LLC4.5729 Reviews
Website View Page
1 Reply
- Lisa PeckPro Member
  OP
  Realtor · San Diego · Member since 2022 · 28 posts · 20 votes
  7mo
  Quote from @Mendell Gosnell:
  
  The sooner the better, but never too late. I invest in Oregon and about 5 years ago started investing in AZ. I think the adage, "live where you want and invest where it makes sense" is some good advice. As you probably know, the first couple years tend to be low cash flow on most deals but over time Real Estate has a great track record. Always depends on your goals. However, real estate provides a lot of options. I am biased of course, but for those who have the aptitude for investing in real estate it is hard to beat.
  All the best,
  -Mendell
  
  Thanks, agreed!
  0 Reply
Garret Rumbea
Inland Empire, CA · Member since 2017 · 151 posts · 79 votes
7mo
Hey@Lisa Peck good to meet you. I'm based out of SoCal as well and one of my partners owns a bunch of apartments in LA area. As a team, we invest out of state in larger apartments. Happy to connect if it makes sense. Always try to connect with investors from SoCal.
1 Reply
Ken M.
Investor · Get yourself trained before doing something inadvisable. · Member since 2024 · 3k+ posts · 1k+ votes
7mo
Quote from @Lisa Peck:

Hello, I'm old and new to investing in Real Estate. I have been a Real Estate agent for almost 27 yrs (IL and CA). Along the way, I picked up a couple of investment properties admittedly (embarrassingly) without underwriting very well. Luckily, I did well on a flip in Northern California and have owned a condo and a townhome in Chicago IL (both LTRs) for a decade or so. Both are in great locations and I have no problems renting them with little to no vacancies and great tenants for the most part but it was unbearably slow to get here. We manage them ourselves (from afar) since we already have people we trust there. I'd like to add a small multifamily (2-4) to our portfolio next. We live in SoCal now and find it difficult to find anything here that pencils out. I have about 9 yrs left before retirement and am looking for advice and debating either a) getting another property in Chicago (cons: tenant-landlord ordinance & escalating property taxes, pros: existing relationships, market knowledge and my desire to visit friends and family there often) or alternate locations I'm considering > Kansas City, MO > Knoxville, TN > Peoria, IL > Winston Salem, NC. I've never been to any of these places. I'm looking for that unicorn with a mix of cash flow (6-8% cash on cash) and appreciation within the next 7-10 years, preferring a location with diverse industries/employment. I prefer B to A- locations. I've got some flexibility in pricing but the numbers need to work (or work within 12 months with a larger upside). I've been listening to Dion McNeeley lately and find him fascinating. I really like his desire to be as efficient as possible owning as few rentals as necessary. I'd love any input!
Always visit the neighborhood you are buying into before you buy.
2 Reply

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