To answer some of @William Collins’ questions and give more insight here’s the plan:I don’t have a ton to put down now which is why FHA is attractive.

But I feel you'll get steadier numbers near year round attractions.

I am looking to buy a property off of 30A, I would say the cost would be around 1 million.

I must have lost about 2 million by selling.

The property is obviously more attractive as a 3 BR and I'd love to be able to buy it as a 2 and rent it as a 3 but don't quite know what to make of the disconnect between the listing and the county records. 

How easy is it to make a $20,000 mistake on an asset that costs just a few hundred thousand, much less on one that is in the millions?

While some properties can be picked up at good prices, turns out in certain areas the proliferation of newer nearby strip malls, more attractive, spacious, copious parking was too competitive.

There is a large market of people who simply don't have the money to pay for a down payment and offering help with that would attract them.

If you've got $ millions sitting with the lender, they will agree to all sorts of neat things. 

From all the podcasts and articles I’ve listened to and read I want to know for sure if my success is likely, or these are just one in a million stories that I wont get to see.