Hes one of the bigger " players" in Ft Myers, also owns ( I assume still does) Social, top " clubs/ restaurants there.

Here's a map showing where 'Short Term Rentals' are allowed: Short Term Rentals Allowed MapVacation Rental - This is the necessary permit for non-owner-occupied STRs in the C-1, RR, R-4, CD, CD-C, CD-M, and CD-V zones.

Quote from @Gash Nookala: David has the right idea about building a team, but the most important player on that team is the property manager.

A 6 month season on this property wouldn’t be the end of the world, as we’ll be working to increase rents, etc to increase the property value before a refi (likely 12-18 month process); however, it would be great to hit an 80% LTV  (instead of 70% LTV) on the exit side of things to cash out myself and all private money 100% after the value add.On this deal, I’m assuming the CD balance is eligible for refinance, since it’s a lien on the property; however, in order to make the 20% down payment eligible as well, should that be recorded as a 2nd lien at the time of closing, or is commercial more flexible/a different beast?

One partner has over 10 years of experience with 2000 Unit, and next one has about 900 units as GP, and the rest of us were first time multifamily players. 

It's vitally important to know who you are working with, and have the history of the players involved.

The current C/D is a mandatory form under state and federal law (every state).So, until states and federal regulators mandate forms for private/hm lenders, you won't see it.

Also Look at Jim Abbott the baseball player. 

You could do that for 3-5% down.. live in it for a year to meet typical requirements for use… then move into a new house, and ‘voila’ - you bought your second (multi-family) rental for 3-5% down instead of 20-25%.It is entirely possible though that you will face debt to income issues on your first rental if your lender wants to see a year or twos worth of rental history before counting your rental income to offset your debt payments…so beware of that.Otherwise you may have to look at creative financing… maybe bringing in a money person where it was a short term investment for them, like “I’ll give you 8% on your money (versus the 4-5,% you could earn from the bank CD) if you will partner with me on this purchase.”

We all know the playbook....teach novice investors how to buy in C/D locations where the cash flow appears higher despite the operating expenses and cap ex being disproportionately greater than better situated real estate.