Well since then, I have been arrested 3 more times and Everytime I go to court, my dumb tresspassing charges get dropped but it's an ongoing thing & the harassment by cops needs to stop.

If it is i am with @Greg Scott  if you have vetted the contractor and they are licensed for what you are doing and you checked references then let the PM know you have selected someone else. 

Then you use those on your personal taxes.

The reality is the opposite - if it's not in writing then the PMC doesn't have to provide the service or can charge extra for it!

We would then bake that charge into the guest's stay.

If they choose to stay, ignore their complaints and then send them a non-renewal notice when the time is right. 

(And best case it was a rental for 17 years then a primary for 3, making only 15% possibly eligible.)Personally, if you and he are both 100% sure of the facts I would first reach out to a qualified intermediary (a person who handles 1031’s).

If you can do that then you have answered most of your questions - essential skills, client relationship, exceeding industry standards, etc.

Then renovate, live there for 12 months and have much of your mortgage paid by the other units.

Ok, so if you are close to a college and a large teaching hospital, then doing 30+ day stays makes sense.