I had originally planned a F&W trip for November of this year just to get closer to the end of Hurricane season. Then free dining came out....
At first I said, no, it's not worth the savings. We went in Sept of 2004 and Jeanne postponed our trip by 2 days (we couldn't get there) but we could extend it by one day on the other end so we only lost a day. We went in October 2005 and left for home the day before Wilma hit Florida. But then I thought about it and here's what I came up with: I booked my trip for Saturday through Thursday so I have some time to play with. If we can't get there, we try to extend the days we lost on the other end. If it comes while we're there, I'm not worried - I've read enough trip reports of people who were there during hurricanes to know it's not the end of the world. If we lost park days I'd see if we could extend our stay by a couple days but if not, I'd just chalk it up and know that we'll be back eventually. If we can't get home because of a storm, I still have a couple days to play with before I have to go back to work.
So as long as my work lets me switch my vacation to that week, we'll be chancing it!