Note: Florida charges a hefty tax on rentals under 6 months. 

Once you file your 2nd year of tax returns, you may now be able to qualify for Agency Loans (FHA/Conventional).

Who is in charge of procurement?

Do you need license like you need to become a conventional loan broker aka originator (I happen to be one, licensed in NY and NJ).

This is what I am encountering, in the current Mortgage Industry.If you think you will go FHA, Conventional, FHA 203k, etc. and then Quit Claim the property, to a LLC, or a Land Trust you run the risk of the lender discovering a Title Transfer occurred and activating the "Acceleration Clause" or "Due on Sale Clause" that requires the loan to be paid in full, within 'x' number of days.

@Tyler Kesling  Adding to the above great points, start with 2-4 units as it's standard conventional financing.  5+ units is commercial and somewhat of a different ballgame.   

And you can provide a good value by charging a lot less than the big operators.

The brother and his son had been living in the house, free of charge, for years, and were gaming the system.

In the last few years, they've made illegal:-Rent controls of any kind-Limiting of fees or screening charges-The ability of HOAs to regulate STRs or LTRs in their neighborhoodThat's just the start.

Conventional 20% down.