Obviously the tenant doesn't have the money to pay rent, so why keep beating that horse to death?  

Sections 8 payments stop immediately on death but today we had a phone call from HUD saying that payments should have stopped once the tenant had been out of the home for 6 months.

I'm probably just worrying this to death.  

The property is deeded to him upon the death of his father.

I love them to death but they are not the friendliest house guests

Do you structure the deal in such a way that upon the owner's death the payments could continue to be made to the heirs or the estate for a defined period of time?  

The fear of death is a strong motivator to move.

When a tenant has a life crisis event, like a serious personal illness or death in the immediate family, we send a card with a love gift. ($50)During extremely cold weather or extremely hot weather we make a personal visit to each tenant to make sure they are prepared for the weather and are keeping safe.Our "All Star" tenants are those that pay their rent on or before the first of the month consistently over time, take care of the property and follow the terms of the rental agreement and our property rules.  

Write up a contract that they get a flat fee, or they do what you don't want to do for a reasonable fee.PMCs are notorious for nickle and diming you do death on all kinds of fees and "emergency" repairs. 

They talk the repair men to death too.