We usually don't book a package. In the past I've bought one a month (family of three)the 3 months leading up to our trip. AAA had pretty good prices when I did that in 2007. Last year I used undercover tourist with the link from Mousesavers monthly newsletter and saved even more for 7 day park hoppers. I saved almost $22 pp off the stated price from Disney. I usually don't book a package because we don't get the dining plan. I've gotten the annual pass before and gotten great rates with the passholder discount. I take a chance on rate hikes to buy the tickets at my convenience (when I have the $$$) but if you can afford to get them ahead of time I say do it. I don't see Disney raising rates in this economy, but you never know.