I have spoken to hard money lenders, but they don't really seem to fund projects destined to be short term rentals.

But Michael is definitely correct in a sense that CT is certainly not a vacation destination in nearly any way besides the Casinos. 

You need to entice people to leave their homes and travel to your rental, and a non-vacation area won't do that as far as I can see.......People in vacation destinations call them “vacation rentals.”

I know the Destin/PCB coastline is a hot market but I feel it might be cooler weather-wise over Christmas?

If you are struggling to find deals in your market, but have the capital and drive to obtain another property, I would research other markets based on your desired outcome- ie, midwest for cashflow, coasts for appreciation and desirable vacation destinations for STR.

In Destin/PCB, we only have so much land and we aren't getting anymore.

I currently have 6 months to 1 more year on my current project and I wont have a better idea how long left until about 1-2 months before and wont know my next destination until about 2 weeks before its time to move.

We went to Destin to look at a property that had incredible AirBnb rental history.

We went to Destin to look at a property that had incredible AirBnb rental history.

Since that’s my planned destination, I think forming a LLC to own the residential rentals and then once I’m ready to move to CRE that LLC has the needed history.