23 years old, looking to buy my first property in 2 years

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23 years old, looking to buy my first property in 2 years

Carl Braxton II
Member since 2025 · 2 posts · 3 votes

Hi All

I am 23 years old, currently living in Tallahassee, FL, but I am from Chicago IL.  I have renewed my lease for another year, so I will be in Florida until 2027.  Over this span of time, I want to position myself to buy a property in Chicago.  By 2027 I will have 2 years of work history at the same job, and I have just opened a secured credit card. I will also note that I am looking to house-hack.

What kind of properties would you recommend me to start looking at (preferably regardless of location)?  

Any areas in Chicago I should focus on, or stay away from?

Should I be concerned with purchasing my first property via an LLC?

Through my continued research, I will better understand what questions to ask, so please give grace

With Gratitude,
Carl Jr.

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Most Popular Reply

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

Great choice with looking to house hack and in Chicago. It's one of the best markets to do this since 25% of our inventory is 2-4 units. I favor the northside neighborhoods because that's where I'm personally closest too plus historically they've appreciated at faster rates than many other neighborhoods in the city.

I'd first focus on where you want to live first and then go from there. If you're trying to live in a place like River north or streeterville, probably not super affordable. However, if you're okay living in more north neighborhoods (edgewater, rogers park) or northwest neighborhoods like Irving park, Belmont cragin, Jefferson park, portage park, you may have more success

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  • Jules Aton
    MD/DC · Member since 2024 · 1k+ posts · 1k+ votes
    10mo

    Hi and welcome! I respect the timeframe so you can fully prepare and it sounds like decide where you want to live for the house hack. 

    0Reply
  • Bruce WoodruffPro Member
    Contractor/Investor/Consultant · San Diego / Phoenix · Member since 2021 · 12k+ posts · 15k+ votes
    10mo

    Solid plan, but I gotta ask......why not stay in Florida? 

    1Reply
    • Carl Braxton II
      OP
      Member since 2025 · 2 posts · 3 votes
      10mo
      Quote from @Bruce Woodruff:

      Solid plan, but I gotta ask......why not stay in Florida? 

      The main reason is because I want to be close to family for the next 1-3 years.  Also, I know Chicago is changing a lot and I want to have property in the city, so I figured I'd get started on that now, and frankly I just love Chicago.  That being said, I'm not opposed to Florida either; if I should direct my attention/energy here initially, for reasons I'm not aware of, please do enlighten
      0Reply
    • Bruce WoodruffPro Member
      Contractor/Investor/Consultant · San Diego / Phoenix · Member since 2021 · 12k+ posts · 15k+ votes
      10mo
      Quote from @Carl Braxton II:
      Quote from @Bruce Woodruff:

      Solid plan, but I gotta ask......why not stay in Florida? 

      The main reason is because I want to be close to family for the next 1-3 years.  Also, I know Chicago is changing a lot and I want to have property in the city, so I figured I'd get started on that now, and frankly I just love Chicago.  That being said, I'm not opposed to Florida either; if I should direct my attention/energy here initially, for reasons I'm not aware of, please do enlighten

      Property prices are lower. Then factor in taxes, both property and income. Then everything else, including politics (they are important  because they ultimately affect business in a huge way)

      https://www.thefloridaagents.com/advantages-to-living-in-flo...

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

      @Bruce Woodruff I gotta say being in Chicago, it's nice not having to deal with hurricanes meaning insurance will be higher. I agree with your other points though that most things are probably cheaper. I will say if you live in chicago and work in chicago, you don't need a car since public transit is good (which offsets some of those savings you mentioned). In Florida, you generally need a car in my experience. 

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

    Great choice with looking to house hack and in Chicago. It's one of the best markets to do this since 25% of our inventory is 2-4 units. I favor the northside neighborhoods because that's where I'm personally closest too plus historically they've appreciated at faster rates than many other neighborhoods in the city.

    I'd first focus on where you want to live first and then go from there. If you're trying to live in a place like River north or streeterville, probably not super affordable. However, if you're okay living in more north neighborhoods (edgewater, rogers park) or northwest neighborhoods like Irving park, Belmont cragin, Jefferson park, portage park, you may have more success

    [email protected]
    Brick House CPAs54 Reviews
    WebsiteView Page
    2Reply
  • Jarret Jarvis
    Real Estate Agent · Chicago · Member since 2021 · 181 posts · 65 votes
    10mo

    Hey Carl, great plan, you’re thinking ahead, which puts you way ahead of most 23-year-olds. Funny enough, I actually helped someone I met here on BiggerPockets two years ago who was in a very similar spot, still in college at the time. He closed on his first condo in Chicago about three months ago!

    You’re doing the right things now: building credit, establishing job history, and setting a timeline. For Chicago house hacks, focus on solid rental demand and low maintenance upfront, think small multifamily or condos near transportation, hospitals, or universities. Areas like Avondale, Portage Park, or parts of Pilsen and Bronzeville have been popular for newer investors depending on your budget and tolerance for renovations.

    Feel free to reach out if you want to talk through financing structure, neighborhoods, or how to prepare while you’re still in Florida. Always happy to help someone getting an early start.

    1Reply
  • Sarita ScherpereelBusiness Member
    Real Estate Agent · Chicago, IL · Member since 2018 · 659 posts · 376 votes
    10mo

    Your first goal should be to understand your budget. Your budget is going to tell you the areas of Chicago you can afford. Then you can decide if those areas are something you want to invest in or if you need to wait to build up more reserves. If you're looking to house hack and use owner occupied financing you will need to purchase the property in your name. A good lender can guide you through these questions and get you started from there you'll need to find a realtor that you want to work with that can talk about the different ROIs of the many Chicago neighborhoods. Best of luck! 

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  • Eudith Vacio
    Real Estate Agent · Chicago & NWI · Member since 2015 · 860 posts · 521 votes
    10mo

    Hey @Carl Braxton II

    You're on the right path by preparing now rather than waiting! I think a couple of questions to ask yourself before you narrow anything down, is what is your primary goal? 
    are you looking more for appreciation or cash flow?

    If your goal is appreciation, you’ll generally find stronger long-term upside on the North Side of Chicago, where prices are higher but demand and resale tend to be more consistent.

    If your goal is cash flow, the South Side of Chicago often makes more sense, as purchase prices are lower and rents can pencil better if you buy right.

    One really important thing to keep in mind no matter where you buy: Chicago’s buildings are OLD. Because of that, I always strongly recommend getting a sewer scope during inspection. Old clay or cast-iron sewer lines can turn into a very expensive surprise if you don’t catch issues early.

    Also, buy in your name - you getter better interest rates + terms + down payment. LLCs are more for experienced investors. 

    You’re asking the right questions early! 

    2Reply
  • James JonesPro Member
    Investor · Collierville, TN 38017 · Member since 2017 · 1k+ posts · 738 votes
    10mo

    You’re actually in a very good position, even if it doesn’t feel like it yet. Time is your biggest advantage right now.

    A few high-level points first:

    • Two years of runway is plenty

    • House hacking is the right instinct

    • Starting with secured credit is fine, you’re early

    • You do not need to rush into anything fancy

    Now to your questions.

    What type of property to focus on

    For a first deal, especially a house hack, keep it boring and finance-friendly:

    • 2–4 unit small multifamily (duplex, triplex, fourplex)

    • Simple layouts, similar unit sizes

    • Something that qualifies for owner-occupied financing (FHA or conventional)

    This gives you:

    • Low down payment

    • Rental income offsetting your housing cost

    • A built-in learning experience

    Single-family can work, but small multifamily teaches you faster.

    Chicago-specific thinking (general, not neighborhood calls)

    Instead of asking “good vs bad areas,” focus on:

    • Areas with stable rents, not speculative appreciation

    • Neighborhoods where duplexes and small multis are common

    • Places with working-class demand and long-term renters

    Avoid:

    • Heavy rehab projects for your first deal

    • Areas that only work if appreciation bails you out

    • Deals that rely on perfect execution

    You want boring and durable, not exciting.

    LLC for your first purchase

    Short answer: no, not for your first house hack.

    • Buy in your personal name

    • Use owner-occupied financing

    • Get the best rate and lowest down payment

    You can always move properties into an LLC later once you scale. Don't let structure slow down action.

    What to do over the next 2 years

    This matters more than the property itself:

    • Build clean credit, one or two cards max

    • Save aggressively for down payment + reserves

    • Study rents weekly so numbers become second nature

    • Learn basic landlord laws for Illinois now

    If you do those things, your first deal will be obvious when it shows up.

    You’re asking the right questions at the right time. Focus on fundamentals, not speed. Your future self will thank you.

    1Reply
  • Wale LawalBusiness Member
    Real Estate Broker · Houston | Dallas | Austin, TX · Member since 2018 · 5k+ posts · 2k+ votes
    10mo

    @Carl Braxton II

    I must say it is really smart to plan early for house hacking in Chicago. From my experience you can do it if you look for 2-4 unit buildings, live in one part and rent out the rest. I recommend you should try to find neighborhoods where people always want to rent and prices are going up, like Logan Square, Portage Park and Irving Park. I suggest you should be careful with places that have a lot of crime or shaky rent prices. When you buy your first property, it is usually best to do it in your own name instead of an LLC.

    Good luck!

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

    Hi There @Carl Braxton II!  Glad to hear you will be coming back to the windy city.  I personally love Chicago, but as @Bruce Woodruff pointed out there are + and - to every market.

    In my opinion, when you are getting started the best market is the one you know the best and can build the best team!  Someone is making good returns (including Chicago, even with the taxes and crime) in every market because of those competitive advantages and others.

    Do figure out what parts of Chicago to look at (keep in mind Chicago is MASSIVE), I think you need ask yourself what type of investing you are trying to do and how you plan to do it? 

    Do you want to house hack?  Flip?  Buy and hold?

    Are you looking for higher cash flow and lower appreciation?  Or vice versa?

    Are you going to hire a PM or self-manage?

    What's your why behind investing in real estate general?  Do you want out of a W-2?

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  • Henry Lazerow
    Real Estate Agent · Chicago, IL · Member since 2017 · 2k+ posts · 2k+ votes
    10mo

    I got my first place at 26. The earlier start the better as can later use the equity for more projects. House hacking works great in Chicago. Some areas: Albany Park, Irving Park, Avondale, Hermosa, Belmont Craigin, Portage Park, Rogers Park. You can cash flow in all these areas on 3 and 4 units if do some cosmetic updates to boost rents and get great tenants. Chicago has really strict tenants rights laws where it takes 8 months to evict so I would stay away from any areas with lower credit tenants even if the numbers look good on paper. My Roger’s Park 4 has never even had a late payment. 

    Also West Town, East Humboldt Park, Logan square can be great if your budget gets you there. Bonus that they are awesome to live during the house hack. 

    0Reply
  • Ethan HaiglerBusiness Member
    Real Estate Agent · Charlotte, NC · Member since 2019 · 111 posts · 58 votes
    10mo

    @Carl Braxton II I would love to assist further. Let me know if you’d like to chat on the phone further. There a lot of great comments from the community here. If you’d like to talk on the phone further with someone, I would be happy to help.

    [email protected]704-607-2078
    3 Little Pigs Rental Management
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