Are the father and son on bad terms?  

We specialize in long-term rentals (7-12 month leases) for properties from 1 to 80 units; single-family, duplexes, triplexes, condos, townhomes, and apartment buildings, that's our bread and butter.

I’d recommend getting terms from private and hard money lenders.

Typically for longer term rentals, but you could try to strike a deal.

IN any case, I would send a certified copy of the new terms to the Housing office along with same copy to the resident; Then I would confirm with the Housing Authority/Resident they received the letter & acknowledge the new terms.

I build duplexes ground up in central Houston for long term holds. 

If you were to partner with another more experienced investor to purchase a short term rental, do a cost segregation, and "materially participate" then you could gain the benefits you are looking for without negatively cash flowing, and you could work out a deal where you maybe only have to materially participate for the first year to claim your tax benefits and then you can act as a more passive investor.

I have a nicely remodeled house in the Highlands , Louisville Kentucky already furnished that I am looking to rent as a mid term rental.

While I'm excited about the potential, I'm also unfamiliar with the specific dynamics of the Orlando market.I'm particularly interested in finding a small multi-family property (duplex, triplex, or fourplex) that would be a good long-term hold.

The simple days of sourcing and acquiring traditional long-term rentals are few and far between.