Pros
Beautiful natural scenery; effective management on Aspen Mountain, overall kind, down to party, varied patrons; unique memories to be made; great benefit of a SKI PASS (>2000USD value/season)...and many more. Aspen is a place that will humble you, whoever you are. This is a good this. One of the best good things, really.
Cons
The humbling might hurt, but again--it's good for you. Would be a particularly challenging environment for those seeking long-term stability (or a sense thereof). The nature of Aspen/Snowmass, perhaps more than many other resort villages, even, is very seasonal by nature when it comes to employment. There are of course year-round, long-term positions for available in the Roaring Fork Valley, but the tend to be more specialized. Those who have the will, however, often find a way--so don't let the superficial barriers to entry keep you away if you feel the mountains calling!