Terrain, terrain, size, nightlife, snowfall, scenery
Sticker shock on everything
It is possible to ski cheaply here if you are willing to completely sacrifice on comfort and if you are willing to give up first chair for turns that might start around 10:30. If you can stand sleeping in your car, and then buying a lift ticket for $20 from some Texan who's all skied out by 11 AM, then you can have a lot of fun here. Now, I'm not suggesting that you do this, but keep the idea in mind because you will be shocked when you see the price on everything in this town. Look to pay next to double on everything from gas to top ramen. Lift tickets don't come cheap either. But, you do get a lot for your money. Best bet is to completely skip aspen and either opt for highlands or jaunt on over to Snowmass. If it is Highlands, you are doing it for the bowl, and that's about it. This is definitely something every skier should do in his or her lifetime, so do it now while you are here. After that, stay in Snowmass. That is where the terrain challenge is.
The real estate maze gets a little old in Snowmass after everything is said and done, so after your legs are done for the day, go back to Aspen where the nightlife is. This is really a great ski town, and it is quite ritzy. In the tradition of Sun Valley, Telluride, and Crested Butte, this is a town that was here well before the ski area came along, so you have some great old architecture and a really centalized feel to everything, unlike the weird drive by feel you have in the interstate resorts like Vail.
These mountains do offer alot, even if the price is not the best.