A common serious issue would be no heat in winter time.

Your story of "bad" financials that banks laugh at is all too common.

So, that suing after the return of the deposit is possible although probably not common. 

I've been at the property a lot in the last couple of weeks, and tenants are telling me that a group of teenagers will bust through the common entry doors and steal bikes and things in the hallway.  

That property is literally screwed.The real answer to your questions is it depends on what is common and accepted in that area.

Rochester has a lot more in common with Buffalo than, say, Troy or the Hudson Valley.If we're getting that specific, there are a few more areas to consider.AdirondaksNorth Country - Watertown, Potsdam, etc.Long Island (very different than NYC)The Finger LakesWith that many regions, I think it's better to just use city names rather than regions.

This is common in my area/Colorado in general especially the ski towns that still allow short term rentals. 

Needs and Wants:What are some common needs and wants that rent-by-the-room tenants face?

No update of common area finishes although clean and well maintained.

This is exactly what the "far right" talks about all the time, except it's not "far right," it's common sense.