I just upgraded to an 05 X2 (205V hull) last fall. Most everyone here will tell you that it is one of the best do-it-all hulls MC ever made. Awesome wake for boarding, even when not sacked out, can be made surfable with additional ballast, and not a bad slalom wake for open water free skiing. You're right, the 205 might carry a $$ premium over the 209, but look at it from the resale angle also. Also, the 205V will have much more family-friendly space than the DD 209. Sooner or later (maybe already!) your kids will also be wanting to bring their friends.
2005 X2, Viper Red, MCX, OJ TZ-X5 prop, PPass, rear 750 sacs, KBS, IBS, Bennett Wake Plate, custom wake shaper
(previous) 2001 X5, 1991 TriStar 190