I'm in the same boat, all my gear is about 5 years old and I love it, but I think getting new gear would be beneficial to advancing my riding ability. Especially since I can get in 40+ days a season now. It depends what your doing, but they have done alott to improve the way boards handle in the last 4-5 years.
I'm keeping my boots since they're comfortable and not totally beaten to shit yet, but I'm getting a 2010 Never Summer Evo-r, and I already bought some Rome 390 Slasher bindings. It's gonna be a sick setup.
PowderHound and TreeNinja