At some point bank has to know their customer and will ask why I get all these $50,000 checks, but no spend. 

A severe reduction in gov't spending is the only path I see. 

Additionally the suburbs have higher taxes compared to Chicago proper.  

Keep the deposit towards additional rent if allowed by law and wish them the best of luck solving their problems. 

I offer them with an additional fee and lease addendum. 

If the building is currently recognized as a single family residence,  then you are changing use and presumably will need to sprinkler the building and satisfy other fire rating and STC rating requirements not to mention the added costs of having to run mechanicals for multiple units, multiple kitchens, additional bathrooms etc.  

I wouldn't necessarily put a lot of efforts into improving/building/spending in hopes of staying booked solid, but it is a nice 'side hustle' for a pretty piece of land to bring in some extra income while it sits. 

If only someone had written a book to help people like you.I prefer you spend some time educating yourself before jumping in, but that depends on how bad the PM is and how quickly you can educate yourself and take control.If you choose to terminate, read your PM Agreement carefully to see if there are any termination penalties.

I always ask within 24 hours of check-in to see if everything is okay-- but I think it takes people time to move in and see if anything additional is needed.

Spend your time on your contracts, insurance, and operations.Contracts-  copy, borrow from someone else as a starting point.