For your specific question about doing a JV on the loan, my suggestion would be that both go on the loan and then do a separate joint venture agreement...because you can not have an LLC on the loan for those loan types, they need to be in your personal names.I am not a lender so maybe one of my lender friends could chime on exactly this would work @Zack Karp, @Michael Facchini, or @Jose Valdovinos?

I know some good people that have went to dinner, had a couple of drinks, drove home, and got pulled over.

I remember working with a client a couple of years ago who wanted to do a 1031 exchange into Phoenix multifamily.. they had some numbers in mind, but no framework beyond “I want more doors.”

They hold their sale in four different locations, and have each locations sales listed separately online. 

Multi-family properties typically draw transient tenants, singles or couples without children, who stay only 1–2 years and cause moderate to serious damages.

I'm also considering a separate living room space or maybe some kind of artist studio. 

We have a couple of exterior photos.Every STR we have stayed at without exterior photos was dumpy.

. - You've got some pretty solid information above and concurrence that it shouldn't cost nearly as much as you thought, but on a separate note, I'd like to understand your situation a bit better.You are currently just looking for a Chicago property to purchase and asking the quit claim question in preparation for closing? 

Maybe a couple per unit.  

I've allowed pets in my STR for five years and haven't had any problems except some extra cleaning a couple times, which was paid for by the guest.