We have cleaned out the three (3) outbuildings and consolidated storage into the upper garage.

We have cleaned out the three (3) outbuildings and renovated one unit and converted to a Short Term Rental as a proof of concept.

Clean and simple. 

But I need to plaster one wall, put a coat of refinish on the nice hard woods and just do general clean up and paint. 

.  ~$1,000/night + $900 cleaning fee.  

There is no guarantee that the building will turn market and should you want to evict a tenant, it can take up to a year under normal circumstances; with COVID, it looks closer to 1.5 years+.Unless you have really deep pockets, like Uncle Scrooge McDuck pockets, hard pass.

@Jonathan Bombaci I like the idea of trying to maximize the proceeds, but even if he moves out willingly I'm left trying to clean/repair/renovate then list and sell a property three states away from me. 

Have your lender call.Make your offers as clean as possible.

You could clean the houses between occupancies. 

It is a single family home in a quiet, residential neighborhood with no HOA and we have a property management company that takes care of it (cleaning, bookings etc.).