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.

@Ryan McGrath I think your first concern is to make sure it's a legal rooming house or to understand the steps that it will take to make it one - which I'll bet would include things like extra egresses and a sprinkler system.One incident / phone call / police visit where word gets back to the building inspector and you might find a big red "VIOLATION" sticker on your front door.Next, I'd want to do some forensic accounting. 

If you do purchase the property then you'll probably want to give the tenants a decent advanced notice of the intended rent increase so they aren't sticker shocked at renewal.

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.  

In addition I’m sure there are plans in the works for composting, recycling, community gardens, and the displaying of various flags and sindry bumper stickers declaring a safe and hate free environment.

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".