If you're really intent on keeping the resident in place then I would just have a conversation with the manager and see what can be worked out, but if they're sticking to their agreement they signed with you, than you might have some decisions to make. 

This is a great learning situation on how to not be passive, knowing your lease terms and local laws, and sticking to your guns when a tenant thinks he runs the show.

One of the things that really sticks with me, regardless of local or out of state is whether you want to be a landlord while working full time. 

Anyone can stick a letter in an envelope and take a pic and say you mailed it but then never actually put it in the mail. 4: The little bit that I have had to deal with stuff like this in court I believe that anything that the opposing party files with the court, not only do they have to send to you as well, but the court upon accepting it then sends you a copy as well.

I think what sticks out to me most is the trade off for time, experience, stress.

Example: someone walking one of our hiking trails and trips on a rock or stick.

Stick to your numbers and strategy but be flexible on the exit. 

sounds like she is trying to stick you before move out.

Should I stick with the more expensive policy until I get the funds to replace the roof or is just best to ask for a loan and replace it now. 

Stick to the lease and provide the correct notifications.