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. 

Cancel your cable and online subscriptions and get rid of your TV2.

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

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.