@Adielle Rivera You should be fine to carry out that situation you mentioned. 

A: "He's fine, but his kid lives in the other unit and is kind of a terror".A: "Yeah" (*quickly covers ash tray*) they don't come around much, and leave me alone, and I like that."

If it was an accident-storm, crack in foundation, etc, I would do the regular checks and rent to them provided you are fine with the pets.

If you're going cash and being conservative I think you'll be fine.

And if you need to rent in short term, that's fine too.  

I'm fine getting reassessed for taxes if needed. 

I would imagine any strong Chicago lease would be fine, but the CAR is something we do. 

I was fine with that as it's peak season now and their lease was through November.

We reached out to the guest but they weren't willing to work with us on it, adamant that they should get to keep the booking.We ended up having to pay the fine and had our listing penalized pretty heavily. 

I'm Eric Whiting from central Florida, passionate about real estate investing and looking forward to learning more and meeting you fine people.