Usually, when a storm gets to be as strong as Dennis currently is, you see some cycling in intensity. However, given how quickly Dennis intensified prior to making landfall on Cuba, and considering how quickly it bounced back upon re-entering the Gulf, I can't help but wonder if the storm will ever do anything over water but intensify. Granted, that's not very logical, but I've never seen such a tenacious storm in my life. From a weather weenie standpoint, it's really something.
While I have doubts Dennis will make Category 5, all it would take at this point is a short period of rapid deepening to bring it very, very close. For that matter, even continued gradual intensification leading up to landfall could bring it close. Of course, Category 4 or Category 5... it's going to be a mess either way.