This situation can be tricky, especially since the guest has been staying since July with consistent two-week renewals.

While I haven't remodeled the main house, it's situated in a highly desirable neighborhood.

For example, I know a lady in my local market that is very successful in the land business and has developed a niche that cashflows very nicely, without a lot of stress, as she puts it though I can't imagine how that is possible. 

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.

Your cash flow situation has just gotten worse.  

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.

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.

. - 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.