He's a driver so also stays in hotels often and isn't at home as much as other people.One benefit of me renting to him is that I was going to leave most of my stuff in the unit to rent furnished and will grab what I am ready to take slowly.

Furnished. 

The purchase price was 395k and furnishings cost about 20k.

He is also willing to furnish a letter from his US brokerage firm to prove he has ample funds to cover for rent and expenses.What would you do?

Do these companies typically handle tasks such as cleaning and furnishing, or would I need to arrange for those separately?

My method to determine this is to do a manual comp analysis of properties on Airbnb and Furnished Finder.

After the current tenant/owner leaves I will go in do a small rehab, furnish and STR following my current system. 

Or, if no minimum lease period is specified, sometimes the bylaws spell out, "A unit owner may not maintain and rent a furnished unit".Happy to discuss my experience.

Maybe try Furnished Finder?

For midterm bookings (1-3 months) we list on Furnished Finder and market the property in Facebook groups designed for travel medical professionals and landlords to connect.