I may be able to help with a few of your questions seeing as I have just moved there myself. The good thing about Whistler is that there is tons of terrain, lots of variety in the people that you will meet, and it's one of the most developed resorts in North America. While this is good in some ways it also works against you when you are trying to move here to work for your first season. Housing is expensive and sparce, it's going to be busy all the time, and everything costs more here. For me, driving out from Toronto took 5 days, I wish I had more time though because exploring is half the fun.
If you are seriously considering moving to a ski resort, Whistler especially, make sure you have researched the job market and accomodations, and save lots of money (more than you think you will need) because down time is expensive (the time in between when you arrive and you start work - the whole terrorist thing has had a big impact on hiring this year).
The Intrawest job fair was held in mid-October and there were maybe 1000 positions available... over 2000 people showed up. I was lucky enough to have experience in the feild that I applied for and had two years of full time work experience. That got me a job but I was still in the second phase of employees to start working - I don't start work till December 8th or so. Besides working for Intrawest, there are lots of jobs in the village to be had but the competition is still super-tough.
As far as accomodation, since I have a job with the mountain I am living in Staff housing on the hill. It's super cheap for anyone's standards ($250/month) but if you don't get in here expect to pay at least $550 per month. Oh, and don't forget that some employers don't offer season passes, that's another $1700.
I just read what I typed and it seems to be fairly negative, but this is Whistler, this is where it all happens and it's going to be worth every sacrifice. If you come here you will meet awesome people, party a lot, and above all you will have some of the best terrain in North America. Just take it from someone who has done it: be prepared financially cuz this is an expensive town. I have met a lot of people that have come out here on a whim with no preparation. Some of them have been lucky, others are on their way back home.
Anyways skiing starts in 3 days and it's still raining. If you have any more questions I have a lot of time on my hands.
Cheers,
Chris