Watching IR and VW loops, you can see a lot of convection firing up SE of the old strong convective core. I think I'm starting to understand this system a bit more than earlier today.

What it seems we have is a very broad, very diffuse system that, due to it's size, is taking a lot of work to consolidate.

Think of past storms: the giant storms always take longer go gain strength and longer to dissipate. Compare that to tiny storms, such as Wilma or Andrew, that blew up from a TD to a Category 5 in a matter of a couple days.

As Dolly is so large, it's going to have a bear of a time getting organized enough to strengthen. but once it does, it's going to take a lot to slow it down (aka interaction with land).

I think the real questions is going to be weather she misses the Yucatan or not. The steering currents are heading mostly westward around tip of Cuba, which should pull her into the Yucatan even if she does try and thread the needle, assuming the steering currents don't change. Given how the shear changed over the past 24 hours, I don't put anything past the winds down there.

For reference, came across this site with a radar loop from western Cuba. It shows the outer bands of Dolly: http://www.cancunweathertoday.com/radar.php