Terrain wise I think Telluride is going to be better. They have actual challenging steeps. A remote location, and less crowds. Plus it's a real ski town.
Vail inbounds doesn't really have that. Fantastic tree runs, big wide open bowls, fun cruisers yes, but Vail is not steep. You can get steeps there but that's out of bounds using the East Vail Gate. Which means you need to know how to travel safely in avalanche terrain, have the gear, and a partner in case it goes south and you need to do a rescue. Two years ago two people died back there in avalanches and both were dug up quickly. So it's serious biz. Not very many safe ways out of there if the conditions are dangerous.
Beaver Creek is just down the road and Summit county resorts are 15-30 minutes away depending on which resort you want to hit. At Telluride, that ski area is really all you get. Silverton is probably close enough for a day trip, but it's a couple of hour drive at least.
Aspen is the party town and with great mountains. Ajax, Snowmass, and Highlands are all great hills. Best scene this side of Whistler. The problem is that it's mega expensive to live there. I know people who rented a one room apartment and one of the beds was in a closet.