Sounds like you are rockin' some pretty old gear. Burton step in binders where the worst of all the step in's without a doubt. That said, I'm sure they still work. If you want to use your gear go for. Tune it up if you think your boards beat. My guess is that what I ride on might be more beat up than your board and I'm not getting a tune for it any time soon.
As far as Aspen goes. It's one of the best in West. By far the most happening ski town there is. Great access to world class mountains. Aspen Highlands is one of the most underrated steep mountains in the West and Highlands bowl is just amazing. Especially if you nail it on a powder day. Snomass is huge and has a little bit of everything. Aspen Mountain, is an Urban gem. You can take the Gondola right out of downtown. Buttermilk, well it kind of sucks, but if you like park, it's the place to go.
Apres wise, take you pick. Tons of great bars and restaurants in town. Expect stuff to be upscale. Even the bums begging for money are of a higher class. If you go you'll know what I mean.