Your first project usually serves as the foundation for figuring out what works best for you since every property comes with its own set of lessons, challenges, and wins.Moving forward, I’d highly recommend getting an inspection, even on off-market deals.

That’s a really solid approach — balancing monthly cash flow with selective profit-taking keeps the portfolio both liquid and growing.

Sounds like you’re approaching this the right way!

We bought it, renovated it to meet sober living standards, leased it long-term to an experienced operator, and then refinanced once the home was stabilized.The challenge was getting the refinance done.

Happy to share what’s working on our end, swap ideas, or even just talk through the unique challenges of higher-end flips. 

As many of you know, finding a condo building that permits short-term rentals in Chicago is extremely challenging due to HOA and city restrictions.I just pulled data on a handful of active condo listings where the buildings explicitly allow short-term/Airbnb rentals.

= Need to look into this Hearing you say this is the most challenging time to determine what is going on in the market, makes me happy to know im learning now at one of the hardest points.

It’s helpful for others dealing with similar challenges. 

Challenges?

As Scott said, there are two different paths and while they are not mutually exclusive, they are different and require different approaches.