New to Real estate investing

Chicago, Illinois
General Real Estate Investing
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New to Real estate investing

Andrew Sangar
Member since 2025 路 9 posts 路 11 votes

Hey everyone, I just turned 23 and want to start buying property asap. I'm from Chicago and I currently do Airbnb arbitrage on a 4bed house in indiana. The place does well so I want to expand and buy a place in the same area with my partner. I had a few considerations in mind...

realtor?: it's my first time buying property so I feel like a realtor might help, but I don't like the idea of paying up to 3% in commission fees (unless she can convince the seller to pay it). 

Expensive or cheap: it's my first place and I don't know if I want to get a cheaper deal but 2 bedroom, but idk if it would pay as well. Or pay 100-200k more and get a bigger unit that I know would do well during fb season. I think I'd be able to expand faster if I get the cheaper unit...idk

location is also a deciding factor - part of the reason my current unit does well is bc it's within walking distance to the college stadium. 

I'd love to hear your thoughts!

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Paul De Luca
Real Estate Agent 路 Chicago, IL 路 Member since 2018 路 1k+ posts 路 1k+ votes
1y

@Andrew Sangar

Working with a good investor-friendly agent is well worth it in my opinion since there's a lot of education and things to know about real estate investing (especially in a particular area). There's a lot that can go wrong if you don't have experience. Oftentimes a seller is willing to pay a buyer agent brokerage commission for the right price.

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  • Jonathan KlemmBusiness Member
    Moderator
    Contractor 路 Chicago, IL 路 Member since 2016 路 4k+ posts 路 2k+ votes
    1y

    Hey hey @Andrew Sangar!   Amazing to hear that you are already crushing it with the AirBnB arbitrage - how did you find the landlord to do it with?

    Do you have the ability to househack a Chicago 2-4 unit property, use a low downpayment loan, or get a renovation loan like the FHA 203k, homestyle, or choice programs?

    Realtor - the right realtor is worth their weight in gold, so don't discount their expertise...you'll find some awesome people to work with here on BP.

    Expensive - Appreciation or cashflow is your real question...what's your current job and plans for the future?

    [email protected]
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    • Andrew Sangar
      OP
      Member since 2025 路 9 posts 路 11 votes
      1y

      @Jonathan Klemm Hey! After I found what market I wanted to focus on, my partner and I cold called and messaged a bunch of landlords and we found a guy with a 50 property portfolio who was willing to work with us as he's planning on selling his units in the near future. 

      I am planning on house hacking around Chicago area as soon as I have enough saved up! I just want to make sure its not in a bad area.

      Since, I'm doing Airbnb, I think id be focused more on cash flow. I've been working a data role for 7-8 months now.

      1Reply
  • Paul De Luca
    Real Estate Agent 路 Chicago, IL 路 Member since 2018 路 1k+ posts 路 1k+ votes
    1y

    @Andrew Sangar

    Working with a good investor-friendly agent is well worth it in my opinion since there's a lot of education and things to know about real estate investing (especially in a particular area). There's a lot that can go wrong if you don't have experience. Oftentimes a seller is willing to pay a buyer agent brokerage commission for the right price.

    4Reply
  • Paul De Luca
    Real Estate Agent 路 Chicago, IL 路 Member since 2018 路 1k+ posts 路 1k+ votes
    1y

    @Andrew Sangar

    To address your second question about getting something cheaper or more expensive - there's always going to be tradeoffs so it's important you be honest about what makes sense for you. 

    Benefits of cheaper properties - you can buy more of them. In theory, your yield could be higher.

    Cons of cheaper properties - Likely to generate lower rents because the area is lower quality. This in turn will generally attract lower quality tenants who are more price sensitive or cost conscious. Lower quality tenants are less likely to maintain your property so that means you could end up spending a lot of money on repairs and turnover.

    The pros and cons of comparably more expensive properties are the reverse of what I stated for cheaper properties.

    Prices, taxes, and rents are good indicators of value but it's not a perfect correlation.

    1Reply
  • Ryan RomingerBusiness Member
    Real Estate Broker 路 Indianapolis, IN 路 Member since 2018 路 340 posts 路 144 votes
    1y

    Happy to see you jumping into the property game! A realtor can definitely be helpful, especially for first-time buyers, but you can try negotiating with the seller to cover the commission. As for whether to go cheap or invest in a bigger property, it鈥檚 a balance between cash flow and long-term growth. If you鈥檙e confident the bigger place will give you better returns, it might be worth the extra upfront cost. Location is key, though, so look for areas with consistent demand, like close to schools, stadiums, or popular attractions. Just make sure to factor in all costs, including maintenance and management.

    [email protected]317-935-0075
    Intrigue Real Estate & Property Management4.6272 Reviews
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  • Tj FlorosPro Member
    Real Estate Agent 路 Chicago 路 Member since 2025 路 95 posts 路 74 votes
    1y
    Quote from @Andrew Sangar:

    Hey everyone, I just turned 23 and want to start buying property asap. I'm from Chicago and I currently do Airbnb arbitrage on a 4bed house in indiana. The place does well so I want to expand and buy a place in the same area with my partner. I had a few considerations in mind...

    realtor?: it's my first time buying property so I feel like a realtor might help, but I don't like the idea of paying up to 3% in commission fees (unless she can convince the seller to pay it). 

    Expensive or cheap: it's my first place and I don't know if I want to get a cheaper deal but 2 bedroom, but idk if it would pay as well. Or pay 100-200k more and get a bigger unit that I know would do well during fb season. I think I'd be able to expand faster if I get the cheaper unit...idk

    location is also a deciding factor - part of the reason my current unit does well is bc it's within walking distance to the college stadium. 

    I'd love to hear your thoughts!


     Sounds like you might want to recreate the Airbnb model here in Chicago. I have realtor referral for a agent who specifically works the Airbnb side of the house, he himself does Airbnb arbitrage and his thing is working with clients who want to buy a buildings to Airbnb. I'm happy to connect you to him if you are interested.   

    [email protected]
    1Reply
  • Eudith Vacio
    Real Estate Agent 路 Chicago & NWI 路 Member since 2015 路 860 posts 路 521 votes
    1y

    Hey @Andrew Sangar 

    that's amazing! where in Indiana are you arbitraging the house? and glad you found someone that is willing to work with you, hopefully you can find a great deal that works for you and your partner + cashflow 馃槂

    realtor?: While recent headlines have sparked a lot of confusion, the reality is that in many transactions, sellers are still offering compensation to buyer agents鈥攅specially when it helps attract more qualified buyers and get the home sold faster.

    Expensive or cheap: a more complicated question that really depends on your feasiblity and long-term goals

    location: I say this is important especially if you want to focus on airbnb

    0Reply
    • Andrew Sangar
      OP
      Member since 2025 路 9 posts 路 11 votes
      1y

      @Eudith Vacio in talks with a realtor currently. Houses are going faster than I expected in the area I'm looking at. Is there a common checklist or things to consider most ppl or you use before buying investment property?

      1Reply
  • Shea Murray
    Chicago/Columbus 路 Member since 2022 路 49 posts 路 50 votes
    1y

    Hey @Andrew Sangar! I don't mind the IDEA of the arbitrage model - but one of the primary ways people make outsized returns in RE is from the equity build, specifically leveraged appreciation. I like your house hack plan better than trying to arbitrage a ton of units, especially as a 23 year old. The power of being young in the RE game means you have a ton of time to let the money compound and weather the ups and downs of the market. These are where you find the stories of the people who bought a 4 unit building for $20k in 1970 and the building is now worth a million. 

     If you go the arbitrage route, you aren't in control of your own destiny, you are governed by the lease which can change at the owner's discretion. 

    Hope this helps! Feel free to connect and DM me if you want to chat! 

    0Reply
  • Eudith Vacio
    Real Estate Agent 路 Chicago & NWI 路 Member since 2015 路 860 posts 路 521 votes
    1y

    @Andrew Sangar - yess! that's amazing. & a checklist in terms of the condition of the property or financial?

    1Reply
    • Andrew Sangar
      OP
      Member since 2025 路 9 posts 路 11 votes
      1y

      @Eudith Vacio both I guess... I my realtor is helping us tour it and get a proper inspection to make sure the property is in good condition. At a glance I know the financials are good but I want to break it down to the details and run the exact numbers 

      1Reply
  • Micah White
    Real Estate Coach 路 Chicago, IL 路 Member since 2020 路 171 posts 路 64 votes
    1y

    Andrew! That's awesome! You're killing it. I'm an Indiana guy myself and love the market. I'd be happy to help you get into your first property here in Chicago. I've acquired 7 so far in the city and have the tools and network needed to get you moving and grooving! Feel free to reach out with any questions you have. Happy to help. 

    2Reply
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