It is cheaper for a Florida resident to buy the cheapest annual pass than it is to visit each of the four Disney World theme parks just once. In addition to the savings on the entry fee, you get free parking. Also, when you pay for a day pass, it's tempting to try to do everything in the park in that one day. First, that's impossible - the parks (especially the Magic Kingdom) are too big and the lines are too long. Second, even if you could do it, you would be exhausted. It is SO much nicer to get there when the park opens (while you can still park pretty close to the entrance and the lines are a bit shorter), spend a few hours and head home when it gets too hot or crowded. Also, by leaving before you have to eat, you don't have to deal with the needed reservations at the ridiculously expensive restaurants. The first time you go and don't pay for parking, don't pay for entrance, don't buy any food and don't buy any souvenirs, you're going to walk out thinking that some employee is going to grab you and shake you by your ankles to get your money. But you get over the feeling.
You're absolutely right about the restrictions on entrance dates. Once you've gone on a weekday, you'll wonder why any sane person would go on a weekend, much less a holiday.
Generally, all this is true for the other theme parks as well. We've had annual passes for Disney, Universal Studios, Sea World and Busch Gardens (they had a bundle sale on those two), Gator Land, Zoo Tampa and the Kennedy Space Center. All were worth doing. The one one park we've NOT done annual passes for (and I'm not even sure they offer them) is Discovery Cove. If you get a Sea World annual pass, you get (or, at least, got) a break on this very expensive but very cool and very exclusive park.
I know folks who keep their annual passes going at Disney year after year after year. I enjoy the theme parks, but that seems excessive to me. We did Disney several years ago and again last year. The other parks we've done just once. We will probably do them again when they've added so many new rides or attractions that we haven't yet seen that it becomes worthwhile again.
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