New to BP. Looking to Connect in Northwest Suburbs of Chicago

[Patryk Ziegler]

Hi BP community! 

My name is Patryk, and I’m excited to be here. I recently joined BiggerPockets and I’m already grateful for all the knowledge, resources, and like-minded people this platform brings together.

I’m based in the Northwest suburbs of Chicago and looking to connect with local investors as I take my first steps into real estate investing. While I’m still in the early stages, I’ve been soaking up as much as I can, reading books, attending meetups, and binge-listening to podcasts.

Right now, I’m at a crossroads.

I’ve been seriously considering two approaches to get started:

• Fix & Flip: The upside of a larger payout is attractive, but I know the risks are higher, especially for a first-timer. I’ve been keeping an eye on local county auctions, and while the deals seem promising, I’m hesitant about making my first purchase in cash without ever walking the property.

  The upside of a larger payout is definitely appealing, and I'd love to build up capital quickly through a successful flip. But let's be real, finding a good flip deal on the MLS is tough these days. There's heavy competition, prices are tight, and most properties are either overbid or don't leave enough margin after rehab.

  I’ve been watching local county auctions too, and while some of the numbers look promising, the idea of buying my very first flip with cash, without walking the property or inspecting the condition makes me nervous. I’m not sure it’s the best move for a first-timer.

  STR Arbitrage (Short-Term Rental): This feels like a lower-risk entry point. The returns may be more modest, but I like the idea of consistent, predictable cash flow and the ability to scale quickly with less capital.

I do have some assets available to invest, and ideally, I’d like to use that capital to build momentum—whether through a flip or cash-flowing STRs.

I'm hoping to hear from investors who've stood at the same fork in the road. How did you decide which strategy to pursue first? Any tips on flipping in the Chicagoland area or building STR arbitrage systems?

I’d love to link up with other investors in the Northwest suburbs—whether you’re flipping, managing STRs, or working on something creative.

Thanks in advance for your insight, and I’m looking forward to learning from and contributing to this awesome community!

—Patryk

[Sarita Scherpereel]

Welcome to the BP community. You should definitely talk with @Daniel Bourdeau He's an airbnb expert in the Chicago(land) market. He's an active investor and agent so he understands all sides of these strategy from his personal and professional experiences. Defiantly check out some of the local meetups. Each will offer a different perspective of the market. @Renee Krystek has a wonderful company that helps with Airbnb strategies as well. Both great people to speak with. 

There will be a lot of naysayers about Airbnb....you just need to know the rules and follow the advice from the experts. The biggest thing you can do is to have a back up plan in case airbnb restrictions get worse for whatever market you buy in. Which means that the deal has to work as both an STR arbitrage and regular rental/flip.

 BP has a section for this under the Real Estate Classifieds- Real estate events & Meetups. Best of luck to you!