I'm not the fair housing landlord expert but I'd probably steer away from referring to it as "veteran housing"Either way I can relate to your situation a little because I also own a house that is shared by multiple people.

. - 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? 

But, here’s a situation in which having my properties in SEPARATE series of an LLC saved me enormous time, aggravation and money.in 2012 I purchased 5 individual high rise condos in different buildings in Phoenix, AZ.  

I don’t know your living situation or if there are any nice 2-4 unit buildings in the area you’re moving to.

You'll want to talk to a local probate attorney to see how much time that could take.If the squatter is not making mortgage payments, you've got perhaps another month or two before the lender begins foreclosure proceedings.In your situation, I would approach the squatter to see inside the property to assess the condition.

But this is a crockpot situation, not a microwave. 

We have dealt with these situations many times.

Simply be a calm stand off landlord who is expecting his tenants to honor the lease - Not you accommodate their personal situation.

For this, I'd recommend being prepared with the terms you're willing to accept in such a situation and staying firm.

You explained "STR arbitrage can be a successful entry point for somebody with the right situation".