Hi everyone! New investor looking to house hack

Hi everyone! New investor looking to house hack

Member since 2025 · 2 posts · 5 votes

Hi guys, I'm Ravi! I'm 23 years old and I've been thinking about moving to Chicago for about a year now. I wanted to live closer to where I work, and enjoy the great benefits of living in the city. I looked into getting a condo but after some more research into that, I found that it wasn't the best decision with lower appreciation potential and high HOA fees. I was ready to rent in the city, but I kept looking for an alternative. After a lot of research and careful thinking on what I want out of this, I landed on the house hacking strategy. I started taking this seriously around August of this year.

My initial goal to move to Chicago has lead me down quite a rabbit hole haha. Over the last few months, I’ve learned so much: how to walk through a property, what are the right questions to ask, local zoning rules, renovation costs, the weirdness of the Chicago market, lending options, and what actually makes a 2-4 flat offer work. And of course shelled out a paycheck's worth for inspection reports to tell me things I should've caught!

I'm still at the start of this journey but it's been super fun and stimulating and of course pretty stressful. I'm incredibly grateful for all of the kind and helpful people on the internet that have helped me so far. I wanted to shoutout Jodi Taylor for her mentorship and for creating the Chicagoland Real Estate Hangout discord channel, and Micah White and the folks over at the Straight Up Chicago Investor Podcast for their amazing content. 


I look forward to connecting with you all and sharing my experiences as I continue my journey.

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Aaron ZimmermanBusiness Member
Accountant · Chicago, IL · Member since 2018 · 2k+ posts · 1k+ votes
10mo
All good areas. You can’t go wrong with any of those. Let me know if you’d like to be connected to any people such as realtors, lenders, etc. happy to provide contact info.
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  • Real Estate Broker · Atlanta · Member since 2024 · 1k+ posts · 608 votes
    10mo

    Ravi, welcome! Sounds like you have done a ton of learning already. House hacking is a smart move, especially in a higher-cost city like Chicago. Wishing you the best as you move forward.

  • Aaron ZimmermanBusiness Member
    Accountant · Chicago, IL · Member since 2018 · 2k+ posts · 1k+ votes
    10mo

    Ravi - welcome! Chicago has an awesome real estate investor community and I'd encourage you to go to the real estate events we have including the holiday party on the 11th.

    What neighborhoods are you looking to invest in?

    • Member since 2025 · 2 posts · 5 votes
      10mo
      Quote from @Aaron Zimmerman:

      Ravi - welcome! Chicago has an awesome real estate investor community and I'd encourage you to go to the real estate events we have including the holiday party on the 11th.

      What neighborhoods are you looking to invest in?

       To be honest, it's been all around town lately. But Logan's the pipe dream. I've found good opportunities in Portage Park, Avondale and Albany Park.

  • Aaron ZimmermanBusiness Member
    Accountant · Chicago, IL · Member since 2018 · 2k+ posts · 1k+ votes
    10mo
    All good areas. You can’t go wrong with any of those. Let me know if you’d like to be connected to any people such as realtors, lenders, etc. happy to provide contact info.
  • Wale LawalBusiness Member
    Real Estate Broker · Houston | Dallas | Austin, TX · Member since 2018 · 5k+ posts · 2k+ votes
    10mo

    @Ravi Thakkar

    Welcome to BP!

    You are on a fantastic journey Ravi and I think by learning about zoning, lending, inspections, and what really makes a 2-4 flat deal profitable, you will perform well. From my experience Chicago is peculiar, but if you buy well, the multifamily properties can significantly reduce your living expenses and quickly build equity. I strongly recommend you to keep learning.

    All the best!

  • Kerlous TadresBusiness Member
    Realtor · Columbus, OH · Member since 2023 · 1k+ posts · 1k+ votes
    10mo

    Hey @Ravi Thakkar, from my experience, house hacking pays off when you get hyper-local, verify rents instead of assuming them, and budget more for repairs than you think you’ll need. Keep walking properties, studying neighborhoods street-by-street, and getting around people already doing it, that’s where the best lessons are picked up. You’re on the right track.

    Kerlous Tadres | Reafco Real Estate542 Reviews
  • Eudith VacioPro Member
    Real Estate Agent · Chicago & NWI · Member since 2015 · 860 posts · 521 votes
    10mo

    Hey @Ravi Thakkar 👋🏽 

    Welcome! Yes, I am super happy that you came to the conclusion that house-hacking is by far, THE BEST strategy! Low down payment, lower interest rate, and you get to live in your investment while it pays you back. Once your equity builds, you can roll into the next property faster than many people expect. Let us know how things go with you and if you need any connections to lender, attorneys, or just a second opinion, I would love to help! I am a pretty big fan of the south side so if you're looking out there, I can definitely give you some advice. 

  • Jonathan KlemmBusiness Member
    Moderator
    Contractor · Chicago, IL · Member since 2016 · 4k+ posts · 2k+ votes
    10mo

    Hey There @Ravi Thakkar!  Great to hear you are getting into the real estate game!

    Sounds like you are on the right track and networking with the right people!  I know @Micah White through the Chicago Cashflow breakfast club.

    What's your game plan and timeline for your purchase?  Any specific areas you are looking?   And what's the top of your purchase price?

  • Real Estate Coach · Chicago, IL · Member since 2020 · 171 posts · 64 votes
    10mo

    Hey Ravi! Thanks for the shoutout man. Would love to help you on your journey in any way I can. Please don't hesitate to reach out! 

  • Specialist · Member since 2025 · 483 posts · 270 votes
    10mo

    Ravi, love the intentional approach—house hacking in Chicago can be a powerful move. Two tips: line up a lender now to see exactly what you qualify for on a 2–4 unit, and tighten your buy box to a couple neighborhoods with clear rent ranges so you can underwrite real listings weekly.

    Which areas are you eyeing for your first hack, and do you have a lender pre-approval in motion yet?

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