To some degree it's always speculation, and to other degrees the risk profile situates itself for it.It's just what are your intentions & pursuits.

@Eddie Gonnella Also, when you are at such a scale, you may be able to fetch a valuation based off of cap rates, rather than a rev. multiple.So it is possible, and it is smart to think ahead in this situation so you don't get stuck with nothing if you want to exit!

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.

If accepting the no parking MTR situation, then the MTR really needs to be pet-friendly (bonus if fenced-in yard) and have laundry (especially in-unit) to make up for the elimination of a key amenity.

Your cash flow situation has just gotten worse.  

I bought the property from a wholesaler that was working with the agents on behalf of out of state family members of the owner who had passed away if I remember the situation correctly.

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.

We have dealt with these situations many times.

. - 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? 

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