It's actually 30 where they cut off the working holiday visa and then there's still ways around it, but thats a whole other story
Let me start off by saying so far I have done two seasons in Whistler and have lived here since October 2011.
First question being, does Whistler sound right for me? I don't want to waste my time with visa's and saving up money only to get over there and hate it. I know a few people who have been and they say they have loved it so I can't see why I wouldn't, plus it's Canada!
Whistler is downright awesome, super chilled, super friendly and bloody honest (hell I've lost my wallet three times and my Iphone 4 and got them all back). It is a great place to live.
Second, how easy is it living in Whistler? I know it's expensive, but how easy is it to find a job? a place to live? to afford rent on a bartender/hotel guest wage?
This is where it gets tricky. If you can get here WAY before November. I would aim to be in Whistler by the start of October at least and come with a good $3000-$5000 to get started and be comfortable. Rent in Whistler is bullshit and most the landlords are out to scam you but you just have to be careful. If you can avoid using craiglist I'd recommend it, but in saying that everywhere I have lived was off Craigslist. You want to secure a job and a place to live before everyone start arriving to Whistler or places will (literally, I have seen it first hand) have a pile of resumes 30cm high. I work as a night supervisor in a hotel so I am able to ride everyday till around lunch time, works for me
Third, should I consider somewhere else in Canada? Maybe somewhere less crowded, more affordable
Can not comment but there are plenty of options if you decide to stay away from Whistler.
Fourth, how is the terrain? I like the odd challenge now and then but I'm more of a steep blue/red kind a guy, some days I just want to be on a easy slope and practice my butters and presses which I'm not confident enough to do on steep terrain yet.
AWESOME! The place is huge. You can find terrain from basically flat to some stupid steep you'll poop your pants.
Whistler is an awesome place, had some of the best days riding here and the best nights out. Overall for a season, as long as you aren't expecting to be able to save while you are here, you will have a BLAST!