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. 

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

Do you think it's best to buy with a licensed, or UNlicensed person?

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.

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