It took them five months to figure out how to properly mail rent to me on time (they've encountered many late fees) and even to this day they pay on the last day humanly possible, but also they leave belongings outside in common space, they leave trash bags outside the trash cans and rodents get into it and tear it apart, they leave a bunch of random belongings and bikes in the foyer (on carpet) and they have filled the basement with what seems like trash.

Hi Guys,So i've been looking into several areas of Chicago and there is something that i cant really understand.I've encountered properties just like this one:1048 W Garfield Blvd,Chicago, IL 60609many properties in the Englewood and Back in the Yards areas...When i analyze them i see that there are "waves" in prices going up and down when the same building can be sold for 30k and then for 250 within each 5 years or so...I also see pretty high rentals there ($1100/m +) ...

As an architect - we encounter this all the time.

and I have encountered something that seemed odd in the process, so I was hoping you guys could shed some light. 

Aside from reading about that disclaimer in numerous forum posts, we've yet to encounter anyone who has actually dealt with the issue firsthand.  

Beyond, the Transient Tax, and potential changes to legislation annually, what are some hidden problems I may encounter?

I guess every business owner who wants to scale up and grow will encounter that "pivotal moment".  

Then I would also have to go through foreclosure and encounter those costs.

I had never heard of this until encountering it in my rental.

Find someone who invests using the same strategy you are and find out some of the issues they have encountered in the past.