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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
Getting started in Chicago real estate investing can feel overwhelming.
There are neighborhoods to learn, lenders to understand, meetups to attend, properties to walk, numbers to run, and plenty of mistakes to make along the way.
In this episode, Tom Shallcross and Mark Ainley sit down with Hart Turner, a Chicago investor who went from zero units to a nine-unit portfolio in under two years. Hart’s story is not about finding one perfect deal or knowing everything before getting started. It is about taking action, building a network, using 5% down owner-occupied financing, learning through real problems, and staying in the game long enough to stack one property after another.
Hart shares how he moved from Los Angeles to Chicago, started leasing high-rise apartments, discovered multifamily investing, bought his first three-unit Greystone in Humboldt Park, partnered on a second building nearby, and then closed on a four-unit Greystone that pushed him to nine units.
For new Chicago real estate investors, this episode is a strong reminder that you do not need to know everything before buying your first building. You need to understand the numbers, build the right network, take calculated risks, and keep moving.
Questions We Answer in This Episode
Q: What’s the housing provider tip of the week?
A: Avoid marketing your rental property on Facebook Marketplace if possible. Mark explains that a lot of rental fraud is coming from Marketplace, and landlords should use better tools, screening systems, identity checks, and verification steps to lower their risk.
Q: Who is Hart Turner?
A: Hart is a Chicago real estate investor and leasing agent who moved to Chicago after spending 18 years in Los Angeles pursuing acting and working in the fitness industry.
Q: How did Hart end up in Chicago real estate?
A: Hart moved to Chicago in 2021 after a friend encouraged him to join her leasing brokerage. He started helping renters find high-rise apartments and quickly learned the city through showings across different neighborhoods.
Q: When did Hart start thinking about investing?
A: Hart started seriously learning about personal finance in 2020, then began studying real estate investing in 2023 after his father passed away and he realized he had an opportunity to buy something for the first time.
Q: Why did Hart focus on two to four-unit buildings?
A: After listening to BiggerPockets and learning about house hacking, Hart realized Chicago has a deep inventory of two to four-unit buildings. That made small multifamily feel like a realistic path into ownership.
Q: What was Hart’s first deal?
A: His first deal was a three-unit Greystone in Humboldt Park on Evergreen. It was an REO property, sold by a bank, and Hart bought it with 5% down owner-occupied financing.
Q: What went wrong during the first purchase?
A: The deal took five months to close because of water and plumbing issues. Hart’s inspection found major drain problems, and the seller ultimately replaced the full plumbing stack before closing.
Q: What mistake did Hart make after closing?
A: Hart tried to furnish two units for midterm rentals, spending significant time and money setting them up. He later realized the units were not the right fit for that strategy and pivoted back to long-term tenants.
Q: How did Hart buy his second and third buildings so quickly?
A: Hart used partnerships. His second building was a two-flat near his first property with a capital partner, and his third was a four-unit Greystone on Fairfield with another partner using 5% down financing.
Q: What is Hart’s biggest lesson for new investors?
A: You have to take action. Hart says you can learn the basics, run your numbers by experienced investors, and get feedback, but at some point you have to buy the building and learn from the process.
Show Notes
02:17 Housing provider tip: avoid Facebook Marketplace rental fraud when possible
04:00 Hart Turner joins the podcast and explains his move from acting in Los Angeles to Chicago real estate
06:45 Why Hart moved to Chicago in 2021 and started working as a leasing agent
11:39 Hart’s personal finance journey and why 2023 pushed him toward ownership
19:08 Discovering two to four-unit multifamily investing and the 5% down strategy
23:58 Hart’s first real estate meetup and why networking became essential
28:29 Deal 1: buying a three-unit Greystone in Humboldt Park with 5% down
33:53 The failed midterm rental strategy and why Hart pivoted back to long-term tenants
38:04 Deal 2: partnering on a nearby two-flat before the first building was stabilized
53:09 Deal 3: winning a four-unit Greystone on Fairfield and negotiating a large seller credit
Takeaways for Chicago Property Managers and Landlords
Rental fraud is increasing, and landlords need stronger verification tools.
Facebook Marketplace can bring extra risk when advertising rentals.
Chicago’s two to four-unit inventory creates a strong opportunity for house hackers.
You do not need a perfect value-add deal to start investing.
A turnkey building can still be a strong first purchase if the numbers make sense.
Low down payment financing creates opportunity, but it also creates thin margins.
PMI, higher interest rates, and vacancy need to be included in underwriting.
Midterm rentals are not automatically better than long-term tenants.
Partnerships can help newer investors scale faster, but financing and roles must be clear.
Meetups matter because almost every useful relationship Hart built came from networking.
Guest info
Guest Name: Hart Turner
Guest Company: Hotspot Rentals
Guest Link: https://www.ihartchicago.com/
Because finding good tenants and property management shouldn’t feel like online dating.
Dear Investor,
If you are an investor in either the city or suburbs of Chicago, I would love to speak with you about how we can help you on your real estate journey. At GC Realty & Development LLC, we help hundreds of Chicagoland real estate owners and brokers each year manage their assets with both full service property management and tenant placement services.
We understand that every investor’s goals are unique, and we love learning about each client’s individual needs. If there is an opportunity to help you buy back your time by managing your rental property or finding quality tenants, please check us out.
Best Investing,
Founder, Partner, Podcast Co-Host, and Investor
