I think we need a Met here. As I'm not a Met.
I think you have a firm grasp of the situation. More than I have at the present. If the ridging you speak of extends/ amplifies SW and E then the Greater Antilles, Cuba through Puerto Rico would return to a setup akin to the one a few weeks ago.
An elongated High pressure ridge from East to West.

I'm sure the NWS personnel have much better data than I have here. And much better computers to view it with. I checked the 850mb vorticity products and then checked the 1000mb surface products. I haven't benne able to look past those 2 products yet.
At the surface...yes, there seems to be an area of precip that moves around the western end of Cuba and into the SE GOM. At the same time the 850mb vorticity loop is indicating a vortice (small scale) in teh same area. But the vortice spins down/ dies/ decays before reaching the western coastline of the FL peninsula. That said. The precip continued to move across Southern FL and into the Atlantic.

WIll wait on the 00Z GFS due out around 04:30Z, or 3 hours from now.
The 00 UTC NAM 84hr products are due to be out around 03:03Z. WIth the rest of the models updated after that.