Looking to invest. Not very many options locally.

Madison, Wisconsin
General Real Estate Investing
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Looking to invest. Not very many options locally.

Jonathon Cornell
Member since 2025 · 10 posts · 7 votes

I have been house hacking for the last 5 years on a duplex that I bought in 2021. My Duplex is currently cash flowing while I live in it. I am looking to expand my portfolio and purchase another property that could cash flow. Where I have hit a brick wall is, there aren't any investment opportunities locally (within one hour driving from me). My question is, should I explore potential investments elsewhere, or is it not worth the hassle? Should I be patient and wait for an investment opportunity near me to open up before I attempt to expand my portfolio? For context, I am 25 years old and feel that I am falling behind waiting for the perfect deal. Thanks in advance.

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Nicholas L.Pro Member
Flipper/Rehabber · Pittsburgh · Member since 2018 · 6k+ posts · 5k+ votes
1y

@Jonathon Cornell

just to challenge you a little... how can there not be any opportunities in a major market like that?

how many properties have you looked at?  how many offers have you made?  how many meetups are going to?  what are you doing to network?  are you looking on and off market?  if you're not looking off market, what are you doing to start looking off market?  can you house hack again if you look for something that breaks even?  what if you looked at 5 properties every weekend for the next 25 weekends?

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  • Nicholas L.Pro Member
    Flipper/Rehabber · Pittsburgh · Member since 2018 · 6k+ posts · 5k+ votes
    1y

    @Jonathon Cornell

    just to challenge you a little... how can there not be any opportunities in a major market like that?

    how many properties have you looked at?  how many offers have you made?  how many meetups are going to?  what are you doing to network?  are you looking on and off market?  if you're not looking off market, what are you doing to start looking off market?  can you house hack again if you look for something that breaks even?  what if you looked at 5 properties every weekend for the next 25 weekends?

    3Reply
  • Jonathon Cornell
    OP
    Member since 2025 · 10 posts · 7 votes
    1y

    Thank you for the reply, Nicholas. "Any opportunities" was likely an overstatement. I currently reside in a very rural area. (Population of 5,000 people) To answer some of your questions, I have been through 20 properties in the last 2-3 weeks and I have only made two offers. I would really like to house hack again because, as I mentioned, it worked out really well for me the first time. I am looking off market and trying to develop connections in my community through talking with other investors and homeowners of single family homes. 

    1Reply
    • Marcus Auerbach
      Investor · Milwaukee - Mequon, WI · Member since 2010 · 5k+ posts · 7k+ votes
      1y
      Quote from @Jonathon Cornell:

      Thank you for the reply, Nicholas. "Any opportunities" was likely an overstatement. I currently reside in a very rural area. (Population of 5,000 people) To answer some of your questions, I have been through 20 properties in the last 2-3 weeks and I have only made two offers. I would really like to house hack again because, as I mentioned, it worked out really well for me the first time. I am looking off market and trying to develop connections in my community through talking with other investors and homeowners of single family homes. 

      I started in 2009 in Milwaukee and by 2015 everything had gotten so expensive that I was convinced it was impossible to find a deal. The type of house I was buying had basically doubled in price. The thing is, from today's perspective 2015 prices in Milwaukee were HALF of what they are today.

      What helped me understand in 2015 was looking at sold listings for the last 6 months in my target area and realizing I would not have been happy with even the lowest prices, so my expectations were to beat 100% of the market - you could call that unrealistic. Today I am happy for every single property that I bought.

      Asset prices are going to continue to go up and probably faster than in the past, because we are entering a phase with generally higher inflation, meaning we are devaluing the dollar faster then we have in the past. 2% are not going to be achievable anymore. Hard assets like gold or real estate cost more when measured in paper money. Real estate prices don't even have to go up, it's just the currency that is going down. 

      Ray Dalio is one of the most successful hedge fund managers of all times (Bridgewater) and explains it very simply - watch:

      debt cycle and history of financial systems

      Interest rates are also going to be higher: boomers retire and pull their money from the stock market. Gen X and Z are not as wealthy and won't be able to fill that gap. Capital is going to be more expensive. You can see that already happening when you look at bond prices, like the 10-year US treasury bond.

      1Reply
  • Aaron ZimmermanBusiness Member
    Accountant · Chicago, IL · Member since 2018 · 2k+ posts · 1k+ votes
    1y

    I would house hack again. The goal is to reduce your housing expense and make sure the property cash flows after you leave. I think it's still possible in Madison Wisconsin although I'm sure it's harder now than in 2021

    [email protected]
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  • Jonathon Cornell
    OP
    Member since 2025 · 10 posts · 7 votes
    1y

    Thanks for the reply, Aaron. I will need to keep an eye out in Madison. Madison is about 1.5 hours away from where I live and work my regular job. 

    1Reply
  • Kate Sanchez
    Member since 2025 · 244 posts · 99 votes
    1y

    @Jonathon Cornell  Great job house hacking for 5 years, that’s a solid start! If local options are slim, it’s definitely worth exploring out-of-state or out-of-area investing. Many investors build systems to manage remote properties successfully (strong property management, boots on the ground, or even turnkey providers). Waiting for the 'perfect' local deal can mean lost time and compounding. If your numbers work elsewhere and you have the right team, it could be a great way to keep momentum going. At 25, you’re ahead of the game!

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  • Jonathon Cornell
    OP
    Member since 2025 · 10 posts · 7 votes
    1y

    Hi, Kate! Thanks for the reply and the advice! I will need to do some more research and really work on building connections! Thanks!

    0Reply
  • Jules Aton
    MD/DC · Member since 2024 · 1k+ posts · 1k+ votes
    1y

    Rural areas are tough but 90mins to a decent area is doable and in my opinion preferable to out of state where you are essentially dependent on others. It might also be worth exploring the offers you made and what happened with them as a learning experience. At 25yo you have plenty of time and while seeking perfection is a losing battle I respect you being thoughtful as opposed to jumping on deals that don’t make sense. 

    1Reply
  • Drew SygitBusiness Member
    Property Manager · Royal Oak, MI · Member since 2012 · 12k+ posts · 9k+ votes
    1y

    @Jonathon Cornell also going to challenge you on your statement that there's nothing in your area.

    How did you find your current home?

    Guessing you bought it off the MLS 5 years ago - when it was EASY to find deals.

    Deals are much harder to find now, so you'll have to put in more effort!!!

    I can't remember the last time we paid asking price or market value for a property.
    - You will NOT make money in this business paying asking or market prices.

    Recommend you pursue two strategies:

    1) Start running the numbers BACKWARDS on properties you like. 
    - Figure out market rents, deduct property taxes, insurance, maintenance, vacancy, etc. and plug remainder into a mortgage calculator for a mortgage amount. Add your down payment amount and that's the MAX you offer! Who cares what the seller is asking, you only buy at the price that makes you money!

    2) Start networking on your favotire social media channel and tell everyone what you do and what you are looking for. Ask if anyone knows someone needing to sell fast. 
    - Keep doing this WEEKLY with different messages and examples.

    You do these two things over and over and over again and you will find a deal in the next 90-120 days.

    [email protected]248-209-6824
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    • Jonathon Cornell
      OP
      Member since 2025 · 10 posts · 7 votes
      1y
      Quote from @Drew Sygit:

      @Jonathon Cornell also going to challenge you on your statement that there's nothing in your area.

      How did you find your current home?

      Guessing you bought it off the MLS 5 years ago - when it was EASY to find deals.

      Deals are much harder to find now, so you'll have to put in more effort!!!

      I can't remember the last time we paid asking price or market value for a property.
      - You will NOT make money in this business paying asking or market prices.

      Recommend you pursue two strategies:

      1) Start running the numbers BACKWARDS on properties you like. 
      - Figure out market rents, deduct property taxes, insurance, maintenance, vacancy, etc. and plug remainder into a mortgage calculator for a mortgage amount. Add your down payment amount and that's the MAX you offer! Who cares what the seller is asking, you only buy at the price that makes you money!

      2) Start networking on your favotire social media channel and tell everyone what you do and what you are looking for. Ask if anyone knows someone needing to sell fast. 
      - Keep doing this WEEKLY with different messages and examples.

      You do these two things over and over and over again and you will find a deal in the next 90-120 days.


       Thanks so much for your reply, Drew. This is great advice that I plan to implement starting today. 

      0Reply
  • Jonathon Cornell
    OP
    Member since 2025 · 10 posts · 7 votes
    1y

    @Jules Aton Thank you for your reply. I plan to continue seeking deals and I think everyone who has replied is exactly right in stating that I need to be putting more low offers out there. Really appreciate this community!

    0Reply
  • Evan Polaski
    Cincinnati, OH · Member since 2020 · 4k+ posts · 3k+ votes
    1y

    @Jonathon Cornell

    First, there is a bit of the mindset component:
    As noted, deals are hard to pencil now in any market.  Prices have not come down meaningfully. During the run up, which it sounds like you came in the middle of, prices were growing far faster than rents.  And now, assuming you are not a cash buyer, interest rates have more than doubled since you bought.  All combined, it does not make for the best investing climate.  So, to your mindset, would you rather buy aggressive with a higher likelihood of losing money, just so you don't feel like you are "falling behind" or would you rather be patient for the right deal that makes you good money?

    To you direct question: out of state investing carries with it a lot of risks, too.  No one will have the same motivations as you.  If you are looking OOS with an agent, they only get paid when you buy, so while there are some good ones out there, there are also a lot that will likely downplay risks just to get you to buy a deal.  Property managers: again, probably some good ones, but I never had luck with the 4 I used.  More work on my part, managing the manager, and making less money.

    As for just throwing out a lot of lowball offers, personally I don't like this approach. So, while I agree with Drew, that most deals are not worth their price, I also don't like wasting my time, or my agent's if I am working with one. So, yes, back into the purchase price like Drew says, but I only do that on properties I like that have been listed for 30+ days on MLS. I don't bother lowballing a new listing, because you will get turned down 100% of the time. Let it sit, the seller get anxious, the agent getting scared they won't make a commission, etc.

    2Reply
    • Jules Aton
      MD/DC · Member since 2024 · 1k+ posts · 1k+ votes
      1y
      Quote from @Evan Polaski:

      @Jonathon Cornell

      First, there is a bit of the mindset component:
      As noted, deals are hard to pencil now in any market.  Prices have not come down meaningfully. During the run up, which it sounds like you came in the middle of, prices were growing far faster than rents.  And now, assuming you are not a cash buyer, interest rates have more than doubled since you bought.  All combined, it does not make for the best investing climate.  So, to your mindset, would you rather buy aggressive with a higher likelihood of losing money, just so you don't feel like you are "falling behind" or would you rather be patient for the right deal that makes you good money?

      To you direct question: out of state investing carries with it a lot of risks, too.  No one will have the same motivations as you.  If you are looking OOS with an agent, they only get paid when you buy, so while there are some good ones out there, there are also a lot that will likely downplay risks just to get you to buy a deal.  Property managers: again, probably some good ones, but I never had luck with the 4 I used.  More work on my part, managing the manager, and making less money.

      As for just throwing out a lot of lowball offers, personally I don't like this approach. So, while I agree with Drew, that most deals are not worth their price, I also don't like wasting my time, or my agent's if I am working with one. So, yes, back into the purchase price like Drew says, but I only do that on properties I like that have been listed for 30+ days on MLS. I don't bother lowballing a new listing, because you will get turned down 100% of the time. Let it sit, the seller get anxious, the agent getting scared they won't make a commission, etc.

      Excellent advise and I agree 100% about not throwing out low ball offers. The bottom line is even if I think things are over priced, which I do now in my area, they are still selling although slower. As long as they are selling I have to accept this is the current value. In the past, and I'm dating myself like in mid 2000s I sat tight and didn't buy anything until they pulled back a few years later. If I had the money lying around I could have purchased a rental that over the long haul would have paid for itself and appreciated but I didn't have extra funds early on. Options might be considering properties that require enough work that the average home buyer can't do FHA but without enough profit for a serious investor. Perhaps find seller financing? There are different approaches and in my opinion waiting for a favorable RE climate isn't a bad one although that isn't the advice I give with regard to total stock market fund index investing. Go figure, lol.

      0Reply
  • Mohammed Rahman
    Real Estate Broker · New York, NY · Member since 2020 · 2k+ posts · 1k+ votes
    1y

    At 25 you’re way ahead of the game just by already house hacking and having a cash-flowing duplex under your belt. That’s a solid foundation.

    Here’s the thing—there’s no single “right” answer. If you stick to only buying locally, you’re at the mercy of your market. If deals are rare, you could sit on the sidelines for years and miss out on building momentum. 

    On the flip side, going out of state opens more opportunity but adds risk—you’ll need reliable property management, strong systems, and confidence in analyzing markets you don’t live in.

    A middle ground might be to widen your radius a bit beyond that one-hour mark and see if nearby metros offer better numbers. Madison is competitive, but cities like Milwaukee or smaller towns in Wisconsin could still cash flow. 

    If you don’t find anything within driving distance, then looking out of state could be worth it—plenty of investors start that way, but they usually succeed because they treat it like building a team (agent, PM, lender, contractors) rather than just buying blind.

    Don’t feel “behind.” You’re 25 with experience and positive cash flow. Be patient for the right deal, but don’t be afraid to expand your search if you can build the right support system.

    Momentum matters, but so does sustainability—you don’t want your second property to turn into a headache that slows you down.

    2Reply
  • Mackaylee BeachPro Member
    Real Estate Agent · Kansas City, MO · Member since 2020 · 1k+ posts · 492 votes
    1y

    I would be delighted to discuss the Kansas City market and provide insights on turnkey properties. The cash flow is robust and poised to assist you in achieving your financial objectives.

    [email protected]
    1Reply
  • Bernice RetzloffPro Member
    Memphis, TN · Member since 2024 · 234 posts · 100 votes
    1y

    Hi @Jonathon Cornell!

    Congrats on getting started early! House hacking that duplex at 21 and cash flowing puts you way ahead of most people your age!

    On your question, a few thoughts:

    Local vs Out-of-state - If your local market doesn't have cash-flow deals, it may not make sense to force one. Many investors expand out-of-state once they've tapped out their local area. The key is building the right team (agent, PM, contractor) so you're not flying blind.

    Patience vs Action - It's a balance. Being patient is smart, but waiting forever can stall your momentum. Sometimes getting into the right market out-of-state is better than sitting on the sidelines waiting on a perfect deal nearby.

    Your Age Is a Strength - At 25, you're not behind at all! You're in a great position. Even if you bought one solid property every year or two, your portfolio would compound massively over the next decade!

    I work as an agent in the Memphis, TN market, and I'll share a quick example! A lot of my out-of-state clients are in your exact situation. They can't find cash-flowing deals locally, so they invest here where entry prices are lower, rental demand is strong, and laws are landlord-friendly. They still get the benefit of long-term application and cash flow without waiting years for a local opportunity to pop up.

    My advice, don't force a deal just because it's local. If the numbers don't work where you are, start researching other markets that align with your goals. Worst case, you gain knowledge and build relationships. Best case, you secure your next cash-flowing property sooner than later.

    I'd be happy to help if you ever set your eyes on the Memphis, TN market! Hoping everything goes well!

    901-664-1949
    1Reply
  • Melissa JusticeBusiness Member
    Rental Property Investor · Phoenix, AZ · Member since 2024 · 518 posts · 1k+ votes
    1y

    @Jonathon Cornell,

    You’re off to a great start - house hacking at 25 and already cash flowing puts you ahead of the majority of people your age. Don’t discount that.

    If deals aren’t penciling in your local market, that’s not a sign to sit on the sidelines - it’s a sign to widen your scope. A lot of investors hit this exact point and scale by branching into out-of-state markets, especially in the Midwest and Southeast where you can still find strong price-to-rent ratios. These markets often come with additional perks too - things like seller credits toward rate buydowns or even cash back post-closing that can give you an immediate advantage on your first year’s returns.

    Of course, OOS investing requires a different skill set - mainly building the right team on the ground. But between solid property managers, vetted contractors, and property source providers who specialize in working with investors, it’s absolutely doable. Many investors grow their portfolios this way while maintaining their W-2 or other businesses.

    So I’d frame it this way: waiting for the “perfect” deal in your backyard could keep you stuck for years, while taking action in a proven cash flow market could accelerate your growth and learning curve right now. At 25, time is your biggest asset - letting compounding work in your favor for even 5 extra years is huge.

    Always happy to chat more about what's worked for other investors.

    Best of luck!

    [email protected]313-221-8718
    3Reply
  • Arman AhmedPro Member
    Real Estate Agent · Columbus Cleveland Dayton, OH · Member since 2024 · 2k+ posts · 929 votes
    1y

    @Jonathon Cornell

    Hey Jonathon, it sounds like you’re in a great spot with your duplex cash flow! Since local deals are limited, expanding into the Midwest can make a lot of sense, especially if you’re looking to grow faster. Many investors focus on markets with strong cash flow, lower entry costs, and solid tenant demand. You can still manage remotely with a good property manager, which lets you keep building your portfolio without waiting indefinitely for the “perfect” local deal.

    [email protected]614-418-6081
    0Reply
  • Stevan Stojakovic
    Financial Advisor · FL · Member since 2024 · 442 posts · 100 votes
    1y

    Jonathon, you’re on the right path. If local deals aren’t penciling out, looking out of market is smart, many investors scale that way. Just be strategic: research the market, line up a good team, and know your numbers.

    Waiting for the “perfect” local deal might cost you growth. At 25, you’re ahead, just keep moving forward with intention.

    1Reply
  • Joe HammelBusiness Member
    Real Estate Agent · Metro Detroit, MI · Member since 2018 · 612 posts · 666 votes
    1y

    Cashflowing on your first househack while still living there is awesome! Since you mentioned living in a pretty remote area, needing to stay there for work, and wanting to househack, you’ve got some fairly tight parameters when you’re aiming for instant cashflow. Right off the bat, your inventory will already be limited since you’re looking for a multifamily property in a more rural setting, so it may take longer for something to hit the market that meets your househacking criteria. The other aspect to consider is that the market has changed significantly from 2021, so finding a househack with year one cashflow won’t be as easy now as it was then. However, househacking is still one of my favorite investing strategies because it’s such a smart long-term equity play. Especially with you only being 25, if you hold on to that multifamily and let it appreciate over time, you’ll gain a ton of equity from that investment. While it’s not year one cashflow, it’s still a great investment overall, which is why the “perfect deal” is so subjective to each individual investor’s goals.

    If your goals right now are more geared towards cashflow, then investing OOS could be a great next move for you. OOS investing can come with more risk, so you’ll need to do your own due diligence to pick a market that best suits your goals, and find a team that you trust to help you execute and provide thorough information about that market. One thing you can do is find a local investor group after choosing your market and gain more insight from locals already investing in the area(s) you’re interested in. As you’re researching markets, it really depends on what your strategy and goals are. For example, if you’re looking for immediate cashflow vs longterm appreciation vs sweat equity, then that will help determine what market will fit your needs the best.

    Anyway, here is some info we put together on the suburbs of Detroit that seems to help when OOS investors are trying to decide on which market to invest in:

    Metro Detroit has what 99% of Real Estate Investors want. Couple hundred bucks a door monthly cash flow, solid ROI, and yes plenty appreciation. (#1 appreciating city 2023)

    I personally make well over $100k/yr cash flow from my portfolio here. All of which, I’ve purchased within the last 5 years.

    There are 2 types of people who dog on Detroit..

    1. People who don't actually own property in Detroit

    2. People who did it wrong and weren't able to execute.

    If you do it right, it’s arguably the best market to invest.

    Purchase: $80k-$130k

    Rent: $1100-$1500 (no rent control in MI)

    1% rule: .9%-1.4% rule deals

    Coc ROI: 4-12%

    Total ROI: 20-40%

    Cash flow: $50-$250/door (after all expenses and budgeting for maint, capex, vacancy)

    Appreciation: 3-10%+ (has been double digit for a decade)

    Location: C+, B-

    These numbers are based on the "sweet spot" in Metro Detroit. These are largely in the suburbs and some markets within the city. You can find higher ROI (on paper) here and probably in other cities…but the probability of actually collecting rent significantly decreases. Where these numbers are found, there is a very high rate of rent actually being paid.

    We have over a dozen Fortune 500 companies just in Metro Detroit with huge Healthcare, Auto, and mortgage industry National footprints. Ford, Rocket mortgage, Beaumont hospitals and more. All complimented with Amazon fulfillment centers, google, and more tech manufacturing jobs.

    The bad reputation of “Detroit” comes from OOS investors wanting sub $40,000, D class properties in poor condition, because they pencil out to 2-3% deals on paper. We don’t buy those.

    We have found what works and repeat it as much as funds allow.

    Detroit has one the highest rent to price ratios in the country…and we focus on the best balance of price/location within the area.

    Here is a picture of my portfolio if you/anyone is curious.

    [email protected]248-422-1685
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  • Jimmy LieuBusiness Member
    Real Estate Agent · Columbus, OH · Member since 2019 · 3k+ posts · 2k+ votes
    1y
    Quote from @Jonathon Cornell:

    I have been house hacking for the last 5 years on a duplex that I bought in 2021. My Duplex is currently cash flowing while I live in it. I am looking to expand my portfolio and purchase another property that could cash flow. Where I have hit a brick wall is, there aren't any investment opportunities locally (within one hour driving from me). My question is, should I explore potential investments elsewhere, or is it not worth the hassle? Should I be patient and wait for an investment opportunity near me to open up before I attempt to expand my portfolio? For context, I am 25 years old and feel that I am falling behind waiting for the perfect deal. Thanks in advance.

    Welcome to BP, Jonathon! First off, you’re definitely not “falling behind” at 25—you’ve already house hacked and are cash flowing on a duplex, which is a huge accomplishment compared to most people your age (or any age).

    When it comes to your question, there are pros and cons to both approaches. Investing locally is always easier in terms of management and oversight, but if deals just aren’t penciling out, sitting on the sidelines too long can cost you growth opportunities. A lot of investors on BP hit that same wall and pivoted to out-of-state markets where the numbers actually worked. The key is building a trustworthy team (agent, PM, contractor, lender) so you’re not the one on the ground handling everything.

    That said, patience is also part of the game—forcing a deal just to get one done can backfire. The way I see it, your options are:

    1. Keep stacking cash and waiting for the right local opportunity.

    2. Start exploring out-of-state markets that fit your investing criteria and learn how to operate remotely.

    Neither path is “wrong”—it depends on your long-term goals and comfort level with managing from afar. If your goal is to scale sooner rather than later, it’s worth at least researching out-of-state markets so you’re ready to pull the trigger when the right deal pops up.

    Quick question back to you—do you see yourself wanting to self-manage long term, or would you be comfortable handing things over to a property manager? That answer can help guide which direction makes more sense for you.

    [email protected]614-300-7535
    Jimmy Lieu, Red 1 Realty4.9120 Reviews
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  • Charles ClarkBusiness Member
    Real Estate Broker · Milwaukee, WI · Member since 2020 · 306 posts · 209 votes
    1y

    @Jonathon Cornell

    Great job getting started early! 🚀 At 25 with a cash-flowing duplex, you’re already ahead. If local deals don’t make sense right now, it’s smart to start exploring other markets—but only where you can build a reliable team. Don’t rush into a “perfect” deal; focus on solid numbers and scalability.

    [email protected]414-719-6090
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  • Corby GoadeBusiness Member
    Investor · Boise, ID · Member since 2014 · 3k+ posts · 3k+ votes
    1y

    You are 25, you aren't "falling behind," most 25 year olds still live with their parents. 

    That being said- everyone thinks nothing works in their market. Are there others successfully investing where you live? I don't even know what market you are in, but I know there definitely are. Their using different strategies and have more experience and resources than you do, but that doesn't mean you should wait- that's not a winning strategy. 

    Just keep house hacking every year or two, but another duplex or better yet, a fourplex and leave a trail of rentals in your wake. If and when rates come down significantly, refi. 

    Just take action and keep going. Don't ever assume it'll get better or easier, take action and take control of your future. 

    1Reply
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