Hard to tell in an application/ screening who is going to be a busy body... 

Quote from @Kelly Schroeder: Investors often mention that speed makes or breaks a deal.

Your experience so far aligns with what I’ve seen: finding financially stable long-term tenants can be challenging, and turnover or lease breaks do happen due to the seasonal nature of the area. 

Probably my fault for not doing my due diligence, but what kept me afloat, barely breaking even was the second floor tenant set the law unit above him.

We have very few break-ins using methods that any experienced management company will know4.

Finding the right team is definitely the make or break factor here, especially with how block by block the city is and how rehab timelines can change fast if there’s no local oversight.There are some solid investor friendly agents and lenders in the market, but honestly the bigger challenge I see people run into is coordinating the rehab phase and making sure the work actually matches the scope and budget.

Love your love for Chicago and I completely agree.Highly suggest you break your post up into several paragraphs...it's tough to read, so I could only make it about halfway through...Regardless, still a huge Chicago fan here!

But my favorite says that tenants can break their lease any time if they choose to buy a home for themselves, and agree to have me represent them in the purchase as their buyer's agent.

They break down inspections, rents, and how the program actually works in real life.

if you can live in it for a few years and then break even when you move out, that's a huge win.