Ernesto should reorganize once it moves away from Haiti with weak shear and an upper-level anticyclone still in place over the system. Upper level outflow is also still strong despite the highly mountainous terrain of Haiti creating a more titled eye. The water temperatures in the channel between Jamaica and Cuba are close to 90F, and this should help refuel Ernesto back to a Category 1 before it makes land fall over Cuba.

How Ernesto interacts with Cuba will play a roll in how strong Ernesto will be before it brazes past the Keys and makes land fall over main portions of Florida. It appears as if the Keys will dodge another hurricane, as I wouldn't expect Ernesto to still be holding Hurricane strength once it comes offshore of Cuba.

Where Ernesto goes after this is still up in the air. The GFDL is the farthest west, showing Ernesto making landfall over the Panhandle as a Category 3. The GFS shows Ernesto making landfall much farther east over Key Largo as a tropical storm. All the other models place landfall in between these two. The farther west Ernest goes, the more time it will spend over the Gulf of Mexico and hence the stronger it will be before land fall.