I work for Vail as a smurf in the wintertime, so here's some things from my experiences:
Employee housing: Lived there last winter, but I only stayed there past December because my roommate moved out after I fought him when we were drunk, resulting in me having my own room for 350/month. A lot of employees live in TR, so there are always parties, but the place is a shithole (we had a mouse named Chad that lived with us all winter) and you may or may not get along with your roommates (I had 2 good ones and 1 douche). Convenience is excellent, because you can hop on the free bus and be at work in 10-15 minutes (you can also do this from non-employee housing, too). If your friends are on board, I'm sure it would be better, but it really is rolling the dice. You will save about 1500 bucks over the course of the winter on housing.
However, Vail did just build a brand new employee housing spot right at the base of the Eagle Bahn, but I know nothing about it.
As for getting a job, unless you secure one in October or early November for the winter, you might be SOL for a solid FT gig but there are always plenty of PT gigs around like serving, retail shops and shit. More stressful than adventurous.
As for the quality of the snow, Vail has a lot of acreage and the park last year was the best it's ever been, and is very easy to lap. The Beav is right next door and Breck/Keystone/A-Basin are all less than an hour away. The backcountry and sidecountry are both very nice out of Vail, The Beav, and Vail Pass, just to name a few. You're only like 90 minutes from Aspen if you want to go see the X Games and the World Cup comes to The Beav early season. Lots to do!