50KalWinter park- Smaller mountain than Vail, more affordable place to live.
Vail- Bigger mountain, Super expensive town to live in and reasonable housing his a long commute(so ive heard).
And someone can correct me if I'm wrong, Dillon I hear is the cheapest place to live in Summit.
Or say fuck it all and move to Crested Butte, Aspen, Telluride, Wolf Creek, Steamboat, Taos, Leadville, or any other ski town where you can get a job. It's November. Prime time for last minute winter hiring.
Oh Aspen is having another job fair on 11/12 at Buttermilk. FYI.
Colorado is expensive in general and there is definitely a correlation to the higher living expenses and better skiing/living situation. Crested Butte, Telluride and Aspen are awesome places to live, work, and ski, but housing is tight and expensive. I'd vote Crested Butte or Telluride in terms of bad ass terrain. Vail is not 10/10 in any category, but way above average when it comes to the whole package of snow, terrain, party scene, decent parks, decent backcountry, good group of locals, and ease of getting to Denver if you want to go see a show or have to fly out of the airport.
Summit County is less expensive than Eagle County (Vail and Beaver Creek), but I'm not super into their terrain, but that's just me! It's also another 1,000 feet up in elevation and can get super windy and cold compared to Eagle County. Most of the affordable housing will be in Dillon or Silverthorne, which is a bit of a drive to the resorts. If you manage to get employee housing in the town of Vail, you are within a 10 minute free bus to work, party, and ski. I don't know for sure, but I would bet living in the town of Breck is cheaper than Vail, but I've heard it's getting more crowded and rent is going up. I love the town of Breck though, just not the resort that much.
Aspen is just awesome. I love everything about it, but you are going to have serious trouble affording housing in the town of Aspen, which means living down valley in Basalt or Carbondale, which is a long drive or bus to the resort. If you can afford it, it's hard to beat Aspen.
Crested Butte and Telluride just have sick terrain with limited crowds. The downsides are not as consistent of snow as Eagle and Summit Counties and you are in the middle of nowhere and it's hard to get to Denver.