An easier route would be to convince him to go in on the short term rental together in a partnership. 

Caulking a bathtub for a plumber is the easiest job he could charge money for, short of charging to lite a pilot light on a furnace or water heater.  

While short-term rentals in areas like Kissimmee, Florida, can pay for themselves and offer lifestyle benefits, the ROI typically doesn’t match what I see from my traditional portfolio of long-term rentals in North Texas.That said, short-term rentals can still be a great choice, especially if you're drawn to the area and the opportunity to combine personal use with investment income.

When a rental is taken out of service for personal use the accumulated depreciation goes away over a short period of time. 

A number years ago, I went to town buying a bunch of rentals in a short period of time and I can assure you they took money from my family instead of putting money in my family pocket.

Find out what financial problem you are trying to solve in the short term until your able to get to more "long term" problems that real estate helps with 

Yep, when we sign up for servicing as a company they ask you "what loss mitigation measures does your company allow" We offer loan mods, forbearance, deed in lieu, short sales and short payoffs.

Purchase price: $785,000 Cash invested: $156,000 Short term vacation rental in Panama City Beach.

Hi AnnaTwo books that you may want to add for your library:1.Short -term rental long -term wealth by Avery Carl2.

Selling before death would be a costly mistake   - you did not explicitly state this was not a multi family but it seems likely from your description.