At this point things do not seem contentious, and having a verbal dialog in person inside the rental unit might give you an idea of where you stand in getting your deposit back.What I mean is showing the pictures in person to the owner while the owner is standing in front of the place the picture was taken when you moved in well before you move out.Good Luck 

Might not explain a large portion of the homeownership numbers, but I have seen friends who will buy property together now and all live there for a few years until one person buys the others out or whatever the case may be. 

Be careful, since this is only for a Person and their primary residence, transferring to an llc may void this.  

I wouldn't want to sell using sub-to personally.  

I still have tenants from that PM who I will need to disburse the security deposits this person stole from me to. 

I am a very experienced foreclosure buyer and I think I can answer all of your questions. I can't get it all into one post, but ask your questions and we'll get to them. 
I started out doing pre-foreclosures back in ...

A huge worry I have is now that he has a huge personal mortgage how would that even factor into the DTI? 

What is my next step (what contracts etc do I need) without involving realtors so I don't have to pay extra fees to this and that person?

As far as your tax questions, I would personally refer you back to your tax advisor or refer you one if you need it.

I personally am in industrial, but Chicago is a 1.2 billion SF industrial market.