He is playing you.

If you have done some work lining up multiple companies you may be able to leverage the competition to get something like this reduced. 90 days is a long time in the rental game.

Although I have accumulated many accolades and accomplishments in my athletic career, I knew that playing a game for a living wouldn’t last forever.

Tenant would like me to use my insurance to pay to have it cleaned up but it didnt hit the home, so my homeowners insurance doesnt come into play.

That being said, it's a numbers game in the end. 

First time the rent is 5 days late, have the property management company have the eviction notice put on the door to start the 30 days.The tenants won't likely be late again when they know you ain't play'n games!

If I waited for that i would never get in the game.

Assuming the amount you're paying is enough to cover the payoff.A short sale would come into play if the amount you wanted to pay doesn't cover the payoff.  

Buy/hold as an existing income seeker or will you be looking more for value play that you can renovate then either hold or flip out of?

Keep in mind you won’t get wealthy on cash flow in this game.