Aspen has a reputation for being the playground of the rich, but it's great whatever your budget. True, your flexible friend can get hurt, but only if you choose to mix with the in-crowd. Aspen is a 19th century boomtown, restored to past glories. It's full of character. Within its cobblestone pedestrian mall beats the heart of the town: shops, restaurants, bars and galleries housed in perfectly restored historic buildings.
Snowmass is a convenient ski-in/ski-out village, 11 miles from Aspen, with all accommodation slopeside or close to it. The two resorts are linked by a great shuttle service, making it easy to stay in Snowmass and still enjoy the experience of Aspen's town.
Aspen Mountain, Ajax, is right in the heart of the town. The other ski areas are a short shuttle ride. Aspen Mountain and Aspen Highlands are full of interest to advanced skiers and intermediates. Buttermilk is great for novices and Snowmass offers a variety of terrain for all skiers and is bigger than the other three ski areas put together. It's one of the biggest and best all round ski areas in North America. The new Chicago-Aspen daily service, which connects perfectly in both directions with London flights, has made Aspen so much easier and cheaper to get to.
You can't go wrong with all the options that the Aspen area offers!