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

The funds are staying within the envelope of the LLC, not leaving the IRA.The provider who put your plan together should be able to assist with this type of conversation.

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'm interested in connecting with other investors and investor-friendly real estate agents, focusing in MTRs in Kansas City.I'm interested in a 2-bedroom house (SFR or duplex), ideally near hospitals and/or universities and research centers.Are there any real estate agents you would recommend from personal experience?

Every person and situation can be unique.