I have a long term tenant who I inherited when I purchased the property he has always called us whenever there was an issue (A/C not working, Broken window, toilet not working etc) Well last night around 8:30 pm we received a call from him that he called a plumber to remove roots from the sewer line and wants us to pay the bill. 

Honestly every one of them will tell you they loose money when they teach renatus classes.  

That's my best advise on it.It is quite common to have issues with permitting or with the removal of tenants so the lender will understand if that's what's going on.

I tried craigslist but my listings keep getting removed for some reason.

Personally I'd disable, winterize, or remove it due to costs of maintenance.  

While there are good operators out there, their will be plenty in this environment of rising rates, expanding cap rates, and not executing their business plans, that will loose all their investors money.

Then roof contractor removed broken skylight in the roof.

The STR use I'm considering would be ideal for this location if the trees/brush are removed.

When the lease ends and a new lease is signed this person can be removed if they have moved out by then.

Hello Nadir,Before I begin management of a property that has a hot tub, I instruct the homeowner to remove it or I will be unable to manage.