ok, here goes.
1. Gonna have some trouble getting discounted anything in Aspen. best bet would be a three day 4 mountain package which is like $200 or so. You can also save a day and hit sunlight mtn, which is MUCH cheaper than aspen and is a really good, uncrowded mountain and only 15 miles from glenwood.
2. must hit areas of aspen include the Highlands Bowl (epic) which is an 800ft vertical hike to the top but 42 degree wide open slope down and is the highlight of the aspen mountains. I'd stay away from aspen mtn itself cuz it funnels down into one area and gets bumped out SUPER fast. Snowmass is the mountain you'll enjoy the most. Its a huge mtn with tons of killer trails that you'll love for your level. I highly recommend these trails: longshot, green cabin (top to bottom 4000 vertical), anything off of the elk camp lift, the campground area, and the big burn. you'll find tree runs, groomed trails, powder, and just about anything else you could want.
3. food in glenwood: juicy lucy's cooks a mean steak, beau jo's has awesome pizza, May's Palace has killer oriental food with everything 1/2 off (recession special), glenwood brew pub has good beer and food, and the bayou does really good creole/cajun. drinking spots are doc hollidays, the springs, the bayou, and loyal brothers lounge. all are right on the main drag and reasonably priced. the first three are mostly chill spots while loyal brothers gets clubby at night. food in aspen: Johnny maguires has amazing sandwiches, little annies has good food and a badass drink special (beer and a shot $3), bad billy's is the burger joint/locals bar, kenichi and matsuhisa are the best with sushi, and zanes has an apres wing special (35 cents/wing). food n drink in snowmass: zanes (again, one at each mtn), brothers grille, the mountain dragon, and the office at the circue. All of these are apres hangouts only. killer breakfast burritos at fuel in snowmass as well.
best boardshops are casual culture in carbondale, D&E at all mountains, and polar Revolution and Radio in aspen.
hope that helps