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 

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. 

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.

This is a 4 day in person mastermind that digs deep into the different aspects of multifamily investing.

I dont post on facebook personally as I cant figure out how it works and or follow it.