whilst not wanting to ruin the vibe of the journey a bit of planning will help make things more enjoyable (the panic of only just finding the rent money wears off after a time or two).
CA: Whistler, huge variety of terrain on one pass, lots of jobs, lots of accom (not always cheap) but staff accom if you are working for the mountain, summer jobs in the bike park, hospitality, forestry, rafting etc.
USA: Any Vail Resort in CO, five mountains on one ski pass (inc A-Basin which means skiing through to Jun), lots of jobs, lots of accom, pretty good staff accom at decent monthly rates, summer jobs on the golf course, in hospitality, landscaping etc.
One point - if you are doing this to gets lots of skiing/ riding then do plan ahead, get a weekend PT ski instructor job at your local hill, get your PSIA/ AASI level 1 (at least, level 2 is better) and get work as an instructor.
If I had $1 for every resort/ local employee that whinged about the amount they worked compared to the amount they skied and 'how lucky I was to ski for my job' I would have several thousand dollars per year to spend on stuff. No luck involved at all, some planning, some hard work and a proper qualification.