You treat them with respect and dignity but set very clear unnegotiable guidelines as to what is expected of them I will usually thank them or show appreciation when they do little things like maybe clean up the hallway or something.

Sure, there technically are still days left... but she is not cooperating, and I need to prepare for worst casehelp-- i have to clean up my mother's mess!

Then we got a letter from a local yard clean up handyman who said he would remove the debris for $300. 

Our other option, I suppose, is to buy a small house with all cash which would deplete all of our savings, which I really don’t want to do right now.

I would like to do this so I don't deplete my seed fund a have stored. 

You could pick up a small MF in somewhere like Lincoln Heights and clean up on appreciation.

Get a thorough inspector.. although a bunch of little things will be noted on the inspection, having it gives you the idea of what you need to clean up/fix.

Not all companies will go onto a 3rd floor roof to lay traps and the one I have found so far that will told me their work, along with trapping and clean up could be up to $6000!!

I agree with @Stacey Paulin, better to start on a system now than to end up with multiple rentals and have a mess to clean up.

Another alternative would be to work with an attorney to draft up a letter asking the tenant to clean up or leave.