Hmm, if the prices are comparable to the Cabana (which my online reading is currently showing) then it looks like Cabana wins for the extra hours, and ablity to walk to the boats for shorter security. Thanks for the feedback!
Looking at airfare, it might be better to have her miss 2 other days of school than the ones she already has off. I don't know if DH will go for that, but it really seems like win win:
Significantly (like $600 savings) cheaper airfare, some fun discounts on rooms that include things like breakfasts at 3 broomsticks and a photo package and stuff, and cheaper rooms. I guess I didn't realize the room rates would flex like that given different dates. It's $184/night when I'm currently looking, but closer to $124 for other nights the week before. Especially with lower crowd levels on different days, I wouldn't even think about the express pass. Seems worth it to me! Hmmm