The home was in rough shape—think mold, a hole in the roof, and years of water damage.

Think multi unit residential, commercial properties, or purchasing houses “subject to” existing mortgage.  

I personally think being a landlord in Chicago is easy and I have never had an eviction. 

I think it's a bad investment.

There was an STR boom when many people bought homes here thinking they could have passive income, but that is not the case here as much as it is in places like Asheville (which is still seasonal, but not as much).

Honestly, it seems like you’ve got more skin in the game than I do since I’m just getting started as a bird dog, but I really admire your approach.I think your focus on tax-efficient strategies and building a reliable team is spot on.

It is very easy to save money working in public accounting.I forgot what my dinner allowance was working at the big four 5 years ago in a major city(I think it was like $20?)

If his landlord reference for the past five years is good, that would weigh much heavier than his eviction.Based on what you've shared, I think this is a low-risk situation, and I would probably accept them with a deposit equal to one month of rent.

Instead of evicting them, i was thinking is there some way that I could rent it back to him for very cheap (mainly to cover just the taxes/ insurance) ie 2k a year rather than the going rate of 2k a month for similar properties.

It’s always great to hear from people who are thinking long-term.