Looking to begin my real estate journey in Chicagoland Area
Emmanuel DiazPro Member
Mokena, IL · Member since 2025 · 9 posts · 2 votesLooking to begin my real estate journey in Chicagoland Area
Most Popular Reply
Aaron ZimmermanBusiness Member
Accountant · Chicago, IL · Member since 2018 · 2k+ posts · 1k+ votesManny - welcome!
Could you start with a house hack? I think that's the best way to break into the market with the lowest risk. If you flip, you're using your heloc and borrowing money which leaves for tight margins plus any income you get from the flip is heavily taxed.
with the house hack, you're ideally reducing your housing payment and getting hands on experience managing a building. Plus, you could one up to every year if you wanted to.
Id recommend going to some local meetups to network with some other investors. I favor Chicago multifamily club and Windy City personally but there's a lot of great meetups. You can also listen to the straight up Chicago investor podcast as well for local insights!
I'm a former house hacker and have a couple properties in Chicago. Feel free to reach out with any questions!
Brick House CPAs53 Reviews
9 Replies
- Flipper/Rehabber · Philadelphia · Member since 2024 · 42 posts · 20 votes9mo
Welcome Manny. Your background is actually a big advantage. With a HELOC, I’d be cautious on a first flip—thin margins + holding costs can eat you alive, especially on deals everyone else is passing on.
In Chicagoland, I’d look at:
• Very small cosmetic flips only if the spread is obvious, or
• Owner-occupied 2–4 units (house hack) to lower risk and build reserves
• Partnering or JV’ing on a first deal to learn without carrying all the risk
Zillow/Redfin are usually picked over—most good deals come from agents, wholesalers, or off-market outreach. Happy to share what’s been working if helpful you can contact me directly!
- Mokena, IL · Member since 2025 · 9 posts · 2 votes9mo
@Michaela Hayes Thanks, Michaela!
- 9moAaron ZimmermanBusiness MemberAccountant · Chicago, IL · Member since 2018 · 2k+ posts · 1k+ votes
Manny - welcome!
Could you start with a house hack? I think that's the best way to break into the market with the lowest risk. If you flip, you're using your heloc and borrowing money which leaves for tight margins plus any income you get from the flip is heavily taxed.
with the house hack, you're ideally reducing your housing payment and getting hands on experience managing a building. Plus, you could one up to every year if you wanted to.
Id recommend going to some local meetups to network with some other investors. I favor Chicago multifamily club and Windy City personally but there's a lot of great meetups. You can also listen to the straight up Chicago investor podcast as well for local insights!
I'm a former house hacker and have a couple properties in Chicago. Feel free to reach out with any questions!
Brick House CPAs53 Reviews- Mokena, IL · Member since 2025 · 9 posts · 2 votes9mo
@Aaron Zimmerman Thanks, Aaron! I would be open to house hacking, however, it'd be down the road, once my kids grow up and move out. Otherwise I feel it'd be too big of a (not so good) change for everyone (including myself) to go from a single family home to house hacking. Will definitely look into the meetups and podcast you mention.
- 9moEudith VacioPro MemberReal Estate Agent · Chicago & NWI · Member since 2015 · 860 posts · 521 votes
Hey @Emmanuel Diaz
Great question — and honestly, you’re not wrong. Prices do feel overpriced right now, especially if you’re thinking about a flip. That said, deals are still happening…
If flipping is on your radar, you will need to be very aggressive with your offers. That means making a lot of low-ball offers, knowing most will get rejected. Eventually, though, someone will budge — especially motivated sellers, stale listings, estate sales, or properties that clearly need work.. Be patient and consistent. The investors still buying today are the ones willing to write 10–20 offers to get 1 accepted.
- 9moAshish AcharyaBusiness MemberCPA, CFP®, PFS · FL · Member since 2017 · 5k+ posts · 3k+ votes
@Emmanuel Diaz, You’re thinking about this the right way, and your caution is a good thing.
From a tax standpoint, just know a flip is active income. Any profit is taxed at ordinary rates, and often self-employment tax too. You don't get the long-term tax benefits you would with rentals, so the deal needs real margin to be worth the risk, especially when using a HELOC on your primary.
If Zillow and Redfin deals feel picked over, they usually are. Most good flip deals aren’t obvious. That’s why first-time flips often go sideways, not because of construction, but because of purchase price and exit assumptions. I’d work with a real estate agent who works with investors. The best ones often know about off-market deals, can tell you when to walk away, and can spot issues you might not see yet. That trust piece is key. Some people also find success by door-knocking or personally walking properties to really understand what they’re buying.
Flips can make sense as a one-time capital builder or learning experience, but I’d keep it small and conservative. Your project management background helps, but don’t force a deal just to get started.
From a tax standpoint, you’ll want to do some upfront research on how the income will interplay with your current situation so you don’t miss opportunities. Depending on the structure and your participation, repairs and maintenance, property management, and professional fees, mortgage interest and points, utilities, insurance, and property taxes, travel, mileage, and home office (when applicable), depreciation, and potentially accelerated depreciation through cost segregation could play a role in your tax situation.
If you want a lower-risk way to start, options like a live-in renovation, a small rental, or even upgrading and renting out your current primary (if you didn't already take out the HELOC) could work with better tax treatment and less pressure.
Good luck and happy to connect!
INVESTOR FRIENDLY CPA®5240 Reviews- Mokena, IL · Member since 2025 · 9 posts · 2 votes9mo
@Ashish Acharya thanks for sharing this! I definitely have to looked at this closer.
- Real Estate Agent · Chicago · Member since 2021 · 170 posts · 64 votes9mo
Welcome, Manny, you’re asking the right questions, and your instincts are solid.
A few honest thoughts from someone who’s seen a lot of first deals:
• Your read on Zillow/Redfin is correct. Most "easy" flips are gone by the time they hit retail portals. If a deal has been sitting, it usually means the margin is thin, the rehab is trickier than it looks, or the ARV assumptions are optimistic. That doesn't mean they're all bad — just that you have to be very conservative.
• Using a HELOC for a first flip can work, but only if you structure it defensively. Smaller projects, shallow rehabs, strong comps, and plenty of buffer for overruns. The fastest way new investors get hurt is underestimating rehab and overestimating resale.
• Don’t overlook other ways to “break in” that are lower risk than a full flip:
– Live-in flip / cosmetic rehab
– Buy-and-hold with light value-add (even if cash flow is thin initially)
– Partnering on a deal where you bring the HELOC + project management and learn alongside someone experienced• Your background in maintenance, reliability, and project management is actually a big advantage. The skill gap for most new investors isn’t execution — it’s underwriting and deal selection. If you get disciplined there, you’ll already be ahead of the curve.
• One quick litmus test: if the deal only works with perfect rehab numbers and top-of-market resale pricing, it’s probably not the right first deal.
BP is a great place to build reps, but nothing replaces walking deals with people who’ve done it before.
If you want to talk through a few real examples or sanity-check flip vs. alternative paths using your HELOC, message me, happy to hop on a call and jam on it.
- Mokena, IL · Member since 2025 · 9 posts · 2 votes9mo
Quote from @Jarret Jarvis:
Welcome, Manny, you’re asking the right questions, and your instincts are solid.
A few honest thoughts from someone who’s seen a lot of first deals:
• Your read on Zillow/Redfin is correct. Most "easy" flips are gone by the time they hit retail portals. If a deal has been sitting, it usually means the margin is thin, the rehab is trickier than it looks, or the ARV assumptions are optimistic. That doesn't mean they're all bad — just that you have to be very conservative.
• Using a HELOC for a first flip can work, but only if you structure it defensively. Smaller projects, shallow rehabs, strong comps, and plenty of buffer for overruns. The fastest way new investors get hurt is underestimating rehab and overestimating resale.
• Don’t overlook other ways to “break in” that are lower risk than a full flip:
– Live-in flip / cosmetic rehab
– Buy-and-hold with light value-add (even if cash flow is thin initially)
– Partnering on a deal where you bring the HELOC + project management and learn alongside someone experienced• Your background in maintenance, reliability, and project management is actually a big advantage. The skill gap for most new investors isn’t execution — it’s underwriting and deal selection. If you get disciplined there, you’ll already be ahead of the curve.
• One quick litmus test: if the deal only works with perfect rehab numbers and top-of-market resale pricing, it’s probably not the right first deal.
BP is a great place to build reps, but nothing replaces walking deals with people who’ve done it before.
If you want to talk through a few real examples or sanity-check flip vs. alternative paths using your HELOC, message me, happy to hop on a call and jam on it.
Will do. Thanks, Jarret!
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