Having been to both, I think I can give you an idea of how they differ.
Aspen's Ski Week tends to attract an "older" crowd that have what I assume are larger disposable incomes. Aspen is gorgeous but it isn't cheap.
Whistler is the opposite. Somewhat "younger" crowds, cheaper and is the place to go if you're a snowboarder. Gorgeous mountains with over 200+ runs. Airfares and hotels will be cheaper. The only downside is the 75 mile, 2 hour ride from YVR (Vancouver, BC) to Whistler. The official Whistler site has some nice package deals that include transfers.
If I had to choose one of the two again, it'd be Whistler.
If you're going to Aspen, I would recommend flying right into to ASE and not DEN/EGE. ASE is 4 miles away from the Aspen resorts. It's about 4 hours (220 miles) from DEN to Aspen and the drive can be treacherous during the winter months. EGE is closer and is about 2 hours (70 miles).
Do also keep in mind that these aren't the only two gay ski events to choose from. Mammoth has a Rainbow Ski Weekend. There's also a European Gay Ski Week (was in the French Alps in 2003). And there's Outboard for the gay snowboarders. Was in Steamboat Springs last winter (
www.outboard.org).
Hope this helps.