If I'm ORL I make that deal before CLE comes to their senses. The supporting cast in ORL is better than the one in CLE. If you think Nelson, Carter, Lewis, Pietrus and Reddick can open looks with Howard's drawing double-teams, think of how open they'll be with the coverage Bron draws. Gortat is a starting caliber center. He's not Howard, but he's no slouch.
As for Bron's incentive, ORL is a bigger market and just think of the marketing $$$$ he could make with Disney and the other theme parks (not to mention the tourism in general) in Florida.
Orlando has a somewhat better supporting cast but it's built around Howard, not James. They'd need to make some moves to win after the trade.
Granted they could make another move or two to add some quality depth but the concept of the team structure is essentially the same. A star player being double-teamed that will either draw a foul or pass it out to an open teammate. Bron's better at both of those than Howard, he just does it from a different place on the floor. Throw in his scoring ability is better than Howard's, ORL is a contender from day one.