The homes next to it are narrow but really deep so that kinda worries me a little bit.

You just need to learn how to operate in your unique REI environment ... the strategies that the Mid-West and Deep South folks employ and preach on BP, just won't work in your market.

I just want to make sure that I'm running as deep an analysis as I can so that I don't get tripped up by something later down the road, if possible.

You can start by jumping in at the deep end and hoping you figure everything out before you drown.  

Sounds like you may want the deal more than they want to clean prior to sell.  

We told him it was going to take a couple months to get his unit repaired (clean up, permitting, scheduling contractor, etc) and he should find another place. 

The basement had trash piled 4-5 feet deep through-out. 

We recently had a case where we contacted the Chicago public health department and they were instrumental in intervention and supportive in our efforts to have the tenant notified that the unit be cleaned or vacated. 

Thought someone might be interested in these deep discount deals.http://www.homedepot.com/SpecialBuy/SpecialBuyOfTheDay?

I have not done it myself, but I think it is a great idea for a bunch of reasons... just make sure your LLCs are squeaky clean.