From Out-of-State to Chicago Homeowner (INTERVIEW)
How to Buy a Home
David Sidoni
4.8 • 859 Ratings
🗓️ 14 April 2025
⏱️ 39 minutes
🧾️ Download transcript
Summary
In just two months, Conan went from renting in Michigan to owning a condo in Chicago—with a unicorn team, 5% down, and a plan built around his daughter and his goals. Buying from out of state? Recently divorced? Facing a competitive market? Conan tackled all of that and more—without overbidding, overpaying, or compromising on what mattered. After losing a few bidding wars, Conan pivoted to a fixer-upper, used his strong credit to keep PMI low, and leaned on his unicorn team for everything from FaceTime home tours to mold remediation negotiations.
This is a story of speed, strategy, and smart choices, with takeaways for buyers who need to move fast, stay flexible, and win in today’s market.
Quote:
“Even after going through a divorce and a money drain, I was still able to buy a home three months later. That just shows—anyone can do this.” — Conan
Highlights:
- How did a divorced dad living out of state buy a home in 60 days?
- Can 5% down with PMI really be smarter than putting 20% down?
- What made Conan pivot back to a fixer-upper—and why it paid off.
- Why FaceTime tours and a “no-pressure” realtor changed everything.
- What’s it like to buy in a Chicago bidding war bloodbath—and still come out ahead?
- How did his unicorn team negotiate mold remediation and pest cleanup before closing?
- What makes condo living with a low HOA fee a smart first step toward ownership?
Referenced Episodes:
- Episode 94 – Real Estate Terms & Definitions
- Episodes 175–177 – How to Win a Bidding War
- Episode 328 – 10 Real Action Steps for First-Time Buyers
- Episode 330 – From Renter to Homeowner With a Home Business
Connect with me to find a trusted realtor in your area or to answer your burning questions!
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Visit our Resource Center to "Ask David" AND get your FREE Home Buying Starter Kit!
David Sidoni, the "How to Buy a Home Guy," is a seasoned real estate professional and consumer advocate with two decades of experience helping first-time homebuyers navigate the real estate market. His podcast, "How to Buy a Home," is a trusted resource for anyone looking to buy their first home. It offers expert advice, actionable tips, and inspiring stories from real first-time homebuyers. With a focus on making the home-buying process accessible and understandable, David breaks down complex topics into easy-to-follow steps, covering everything from budgeting and financing to finding the right home and making an offer.
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Transcript
Click on a timestamp to play from that location
| 0:00.0 | Yeah, it's a bloodbath out there trying to buy your first home in 2025. And don't take my word for it. |
| 0:06.0 | This episode is Conan, an interview with him. He closed on his home in 2024 in the Chicago, Illinois area. |
| 0:14.0 | Now, he's a divorced dad and he wanted to move closer to his daughter. His story has valuable lessons on buying a home in less than two months. He used a 5% |
| 0:24.2 | down payment and was totally fine with the PMI, thanks to his good credit, kept his PMI score |
| 0:30.1 | down very low. He's also got tips on buying in one state while you're living in another one. His |
| 0:36.0 | realtor actually helped him out by doing |
| 0:37.8 | FaceTime home tours with him. And he also has tips on how to do remote neighborhood reconnaissance |
| 0:43.3 | while you're not even in that state. He tells you his reasons why he actually ended up pivoting back |
| 0:49.5 | to a home that he had originally passed on. And he did the math and found out that he got a better deal |
| 0:54.9 | with a fixer upper instead of a turnkey home. And then, of course, with a fixer, you're going to get |
| 0:59.3 | some tips on how to deal with home inspection issues like mice and mold. And you'll even |
| 1:04.8 | hear Conan say something positive about HOAs and buying a home with those people. Yeah, that's interesting. This is a pretty |
| 1:13.5 | awesome story. Let's check it out. How to buy a home educates, protects, and connects first-time |
| 1:19.5 | home buyers to qualified vetted realtors in their area, whether you're looking for DIY |
| 1:23.3 | information or step-by-step guidance. How to buy a home is the number one resource for first-time |
| 1:28.0 | home buyers. All right, homies, it's interview time. I'm very excited. Conan bought a home in the |
| 1:36.1 | Illinois around Chicago, and he's got an incredible story. So you know the drill Conan. Before we |
| 1:43.7 | start the story, give us your number one tip. |
| 1:46.7 | Number one tip is definitely to trust your unicorn, which is like your team, like your |
| 1:53.3 | realtor and your and your loan officer. |
| 1:56.7 | They really helped guide you. |
| 1:58.5 | Like they were definitely a teacher. |
... |
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