Looking to begin my real estate journey in Chicagoland Area

[Emmanuel Diaz]

Hello everyone,

I'm looking to begin my real estate investing journey using a HELOC. My original goal was to buy rental properties, but I haven't been able to find anything I can afford using the HELOC alone. As an alternative, I'm considering doing a small flip to build cash reserves and gain experience.

My hesitation is that, aside from projects on my own home, I’ve never flipped a house. Most of the properties I’m finding on Zillow and Redfin seem either overpriced or have been sitting long enough that experienced investors appear to be passing on them, which makes me cautious about pursuing those deals.

I’m hoping joining BP will help me learn from others and build connections. My professional background is in maintenance and reliability within manufacturing, so I bring experience in project management, budgeting, and data-driven decision-making.

I’d appreciate any advice from those who started in a similar position—especially thoughts on whether a first-time flip makes sense here, or if there are better ways to break in.

Thanks,

Manny

[Aaron Zimmerman]

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!