There are lots of jobs in Whistler....I would worry more about accomodation. There is a STRONG lack of accomodation around there. Getting a job is easy enough...it's just finding an affordable place to live that will be a challenge.
You could live in Squamish...it's about an hour away and now that they fixed up the Sea to Sky highway for the Olympics it's a better drive and maybe a bit faster than it was wayyy back.

EDIT: YES it's definitely cheaper to get your gear there. There's soooo much of it and if you get a good sale or something used you could get a great deal. Also stuff like jackets and stuff are a lot cheaper there.