Challenges?

You are after a door handle that is always in the locked position or rigid.  

This article might be helpful, but isn't considered 'official legal advice' https://www.nolo.com/legal-encyclopedia/handling-t....What I would do depends on what stuff is in the apartment.

I will definitely check into whether or not AirBnB handles the taxes - would hope so as that would be the ideal scenario. 

I would surely use this towards buying a deal if I needed to and handle emergencies with a credit card if necessary.

If you can provide a solid wall of defense, you realize that most attorneys realize how challenging it will be to bring litigation against you and will look for the next guy who has all his properties in his own name or in an LLC with his name written on the title.

My wife has strong managerial and book-keeping skills and could likely handle GCs quite well.

Im looking for some information regarding the following.Every market has their obstacles and challenges.

I personally think that Rent Control will literally kill the city's rental market as well as force investors to look elsewhere thanks to the fact that Chicago is already a challenging place to be a landlord. 

Another thing, I think how you handle pre-screening and having tenants pay for applications is market dependent.