And, the best you have given is that you want $4k because they didn't communicate to you in a timely manner?

Within the U.S. if you want to avoid the bureaucratic nightmares that often follow STRs you will probably want to invest in a well established STR market that already has laws favorable to STRs.

However, a lot of concerns can be mitigated with looking at their past rental behavior in a lot of different settings.

If that co-signer isn't in a position where you can force them to pay if things go sideways, then the fact that they co-signed is just a promise and you can't cash a promise!

I just realized that section8 and forcing the value in a home "FOR RIGHT NOW" is not for me.

Are you interested in a specific startegy (brrrrs, flips, vacation rentals, etc)?

If you are considering this approach, I suggest you buy an A-class property in a landlord friendly city and get a PM.

I am still living in Chicago but plan to move to New York in a year or two.

We live in a litigious society and people are sadly looking for ways to either get something for free or more. 

It's a really sexy application on webinar, but even for the "Get It Now" price may not be worth it if you can't shut it off in a timely manner.