It all depends on where it crosses Cuba... I haven't seen the new 5AM map, but if it crosses at a 'fatter' place, there will be more reduction in intensity than if it passes nearer the tip. But, the thing about interactions with land, is that intensity reductions are more caused by a reduction of the latent heat of condensation, more so than friction. So, while the mountainous area may have more of a frictional effect than flat land, that's not the overriding factor. If it crosses back quickly into warm water, the loss of latent heat will be minimized and it can restrenghten.

Ok, now I've looked at the 5AM map... not much of a shift, just to the extreme west tip of FL (i.e. the FL/AL border)... not much change over Cuba, it appears. Strange.... you'd think they would have shifted the Cuba part more and not the FL part based on the discussion.