All Forum Posts by: Victor So

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

Hello all, 

I'll be in the position to make my first deal in about 3 months, so I'm planning how to finance it. I want to do either a simple fix and flip, or a multi-unit house hack BRRRR. Either way, I will get an FHA for the 3.5% down, but I'd like to do a FHA 203(k) so I can use leverage on the rehab and not have to go completely out of pocket.

Have any of you done this, or do any of you have any words or advice for or against doing this? I greatly appreciate any help!

Thanks,

Spencer

Hey BiggerPockets!

I'm a motivated first-time investor and I'm just getting started on my real estate journey, with a primary focus on House Hacking in the Chicago Suburbs. I'm actively looking to build a strong network of professionals who I can partner with for success.

I'd love to connect with:

- Lenders familiar with investment-friendly loan options (especially for house hacking/owner-occupied properties)

- Real estate agents who work with investors and understand the local multi-family market

- Contractors or handymen experienced with value-add projects, rent-ready repairs, and property maintenance

If you're open to chatting or have referrals, please feel free to drop a comment - I'd love to connect, learn, and see how we might work together.

I'm looking forward to meeting some great people here!

Hey all — just wanted to share some quick thoughts from my experience running a short-term rental here in Chicago and why I think more people should be paying attention to the Midwest.

I’ve been house hacking a 2BR in-law unit in Portage Park (NW side, not touristy) for the past 2.5 years. It pulls in about $32k a year, covers most of my mortgage, and has been a great way to build wealth without having to go full “Airbnb mogul.” I also manage some Luxury ground up builds in Colorado, but this is my 'live for free' strategy.

Here’s why I think this kind of setup works really well here:

1. Chicago’s tough rules actually work in your favor
Chicago's short-term rental rules are strict — licenses, insurance, 2-night minimum, ect. Most important: in most cases it needs to be your primary residence (unless its in a larger building with less than 25% currently as airbnbs AND legal in the HOA). That knocks out a ton of out-of-town investors

A lot of hosts fake the “primary requirement” thing, but they’re technically breaking the rules. Since I actually live here and rent out the lower unit (which isnt technically another 'unit', I’m 100% compliant — and I’m not competing with a flood of illegal or high-volume operators. Way less saturation if you do it by the book. I will say it looks highly lucrative for the investors renting out 5/6BR homes with solid amenities, although legally dubious and not possible to launch multiple listings. 

2. Midwest pricing still makes sense
Compared to places like Florida, Texas, or Tennessee — where inventory is surging and it’s turning into a buyers market — Chicago’s still solid. Inventory is super low here, which is keeping upward pressure on prices. Reventure.app is forecasting about 5% appreciation in 2025, and we’re still in seller’s market territory. That stability gives me confidence in the long-term value of the property.

Plus, entry prices here are still reasonable, and the rental demand is strong enough that the numbers actually pencil out. That mix is getting harder to find.

3. There’s demand, even outside the “hot zones”
I’m not in downtown or a trendy area, but I still stay booked. I get tourists, business travelers, folks visiting family or coming in for events. It’s steady. Summers are obviously busier, but winter doesn’t completely die — I’ve learned how to price and plan for the seasonality.

If you’re thinking about getting into STRs and like the idea of house hacking or finding something low-key that still cash flows, I think Chicago (and the Midwest in general) deserves a look. I’m a local realtor alongside a property manage and help people find these kinds of setups — happy to connect if you’re looking into it.

Anyone else running STRs in less obvious markets? Would love to hear what’s working for you.