Still, my soft heart left my head feeling pretty rough, like a "failure".I don't think with your experience and 17(!)

Managing a good STR is pretty easy.

I was fortunate enough to find a lender with 15% down for my previous properties  For sure, man, I’m sure it varies by state with Lending  but in Texas 20% down is  pretty standard on investment properties.

Check out this recent thread on LLC’s, it’s pretty eye-opening that of all the very experienced investors on here, with centuries of investing experience combined, the consensus was that LLC’s are not needed for most investors:  https://www.biggerpockets.com/forums/926/ Of course gurus will tell you that you need one before you even have a single property, because it makes them sound smart.

Credit Unions are pretty great, as in my experience, commercial loan renewals tend to be automatic.

The area has certain advantages like shelter from regulation risk (pretty much as low as anywhere in the country if you buy in the approved STR tourist zones) and long term security (people aren't going to stop going to Orlando anytime soon). 

I have heard there are FHA construction loans but that they are pretty restrictive and do not allow for multi unit construction.

As other people mentioned the areas do change pretty quickly. 

I'm also pretty handy and would be open to purchasing a property that requires some minor work before tenants can move in.

Unless you want to continue having negative cashflow, you pretty much have to raise rents.