Ok, along with other people here, I've spent a good time in whistler.
I went there alot, every summer for glacier skiing and training camp since my early moguls days. Last summer I actually drove down with in mind to stay a little longer, ifnd some work...etc...
Lucky was I, found a good and cheap place to stay at first, got there in may.
Chilled out, visited, etc... skiing started, friends got in town. Yet, no Job. but lots of fun. Thanks to the big chunk of cash I had when got there. then, thanks to a good landlord, and thanks to Visa as well. I ended up getting a job for a store in the 4 season in august when all friends were gone but I decided to stay longer.... 4 Seasons is exactly the place you want to work at. They pay fairly well, and you have access to staff cafeteria, free when you work, cheap when you dont work, but damn, the best food I ever had.
1- do no say " I will get there in september and see what happens" You will, yes YOU WILLL get screwed.
calculate this, let say you find a cool place for 400-500 in june, and get it for a year. 12 X 500=6000
If you get there in september, you skipped 3 months, but wont find something decent under 650-700
650X9= 5850
Just rent earlier even if you arent here... even july will do it, and save you 500... but in the long run, you will more than just that anyways...plus, getting there in the summer will get you more job opportunities, and you will be able to choose where you live and where you work, instead of getting "What's left".
Pm for any advices.