You will need to learn how to run comps, figure out what rents are in the area and build connections to PM's, GC's, etc. 

On a good note, my current flip is on the money!

I just bought one of their zero money down SFRs in alabama last year. 

You have a different kind of short term rental, and you are there. 

So for a $500k investment you would look to raise $250-$300k and get bank money for rest but your overhead will be too high.

So while every market is different and $4500/mo in rent is nice, are you spending a lot of money to have a less valuable property, versus spending that same $400k (or less) to do a nice renovation and keep it single family home and sell it or rent it out as a nice single family? 

I have never seen someone throwing every one of the fashionable strategies into a single short paragraph.

I’m about 4 years from retirement and regretting not venturing into this world sooner.I’m currently going back and forth on whether to focus on short term rentals in Florida (Destin, PCB) or long-term single family homes in the Birmingham, Al area.

Nice, what's the next move to create multiples on the money earned from the sale? 

Do I go with a Hard Money lender until I can refinance into a Conventional loan?