Hi there,I own a handful of longterm rental properties in Chicago and have sat on an HOA Board for many years. After years and years of being frustrated by how tough it is to find honest, communicative contractors, I ...

Would love to pick your brain over dm.

If I had to leave a takeaway from this post before getting too far in it would be that whatever goals are had you have, we have these goals for a reason and typically it does not go exactly as planned but even if it doesn't go as planned, we can pick up where we left off and give it a fresh start.

It kind of feels like the rest of the market - you kind of have to pick a lane between cash flow and appreciation. 

This property only needs a pool and furniture to get it to spectacular status.

Thanks for touching base and let me know if there's room for collaboration on any of your projects or just willing to share lessons you've picked up along the way.

Not a huge increase in cash flow, but you're picking up another appreciating asset. 

Quote from @Garrett Brown: Quote from @John Underwood: Nothing that paying for a 3rd party app to automate functions will fix.If I had to pick something it would be getting higher occupancy rates.Overall things are great.I'm definitely not an app developer so no worries about me making one that can help.

Furniture is another story; we have tons of suppliers.

My "middle" is close to my bottom price and I picked up another $75,000 of free equity, for a total of $198,000 free equity in 5 days on two properties in 2025.