OK, I lived in Vancouver from '97 until '04 and have much to say on the topic. If you do go, let me recommend living close as possible to Commercial & 1st. It's a great neighborhood with lots of open-air produce marts, plenty of cheap groceries, and endless cheap take-out possibilities. I get homesick just thinking about it.
Out of a metropolitan population of over 2 million, the number of snotty hipster assholes is only a few hundred—though I will take this opportunity to mention I've been listening to The Smiths since '89. Which is why, to my ears, they're played the fuck out. Anyway, like everywhere else, there are cool people and total douchebags. During my time there I met plenty of über-friendly, easygoing persons that certainly reinforced the laid-back west coast stereotype. (In my own experience, Canadians are, overall, much snottier than Americans anyway.) I have endless stories about pushing around on my skateboard and making new friends instantly—especially girls.
Nowhere else in Canada can you count on enjoying a few sunny, 9°C January days where you can shred in a T-shirt. Sure there's Victoria, but its sleepy reputation isn't for nothing. When you're bored on a Friday night you can always count on a party on the 800 block of Granville. Vancouver's downtown is one of North America's best (I can say this with authority having visited or lived in nearly every major Can/Am city) and will only get even more live when the Canada Line subway/elevated Granville/Cambie/Richmond/Airport train opens this year.
Vancouver's done a great job with city planning considering what a drab shithole the place was in the 1970s. There are lots of happening storefront-sidewalk districts—Broadway and West 4th in Kitsilano, south Granville, Cambie, Main Street, etc.—which is the best measure, in my opinion of any city's value.
I live in Toronto now. It's a true cultural mosaic but it fails to coalesce into an identifiable civic psyche. There are vestiges of the old, WASPy Toronto, but the new Toronto can be defined more as a pastiche of ethnicities under the umbrella of Canadian neurosis. Toronto fancies itself as Canada's answer to NYC, but it's not even on a par with Chicago. The plain brick architecture—with those hideous 1970s horizontally sliding windows—along the former's commercial streets is crude and cheap compared with the impressive terra cotta, bay windows and intricate cornices of the latter.
In that respect, Chicago and Montréal are more similar. Of the three Canuckistan metropolises, Montréal is without a doubt the most flavorful—and, as an added bonus, enjoys the lowest cost-of-living. The skate scene there is robust, yet still impeded by the same issue that vexes Toronto and, to a lesser extent, Vancouver—winter.
Still, if life on four urethane wheels is your thing then there's nowhere else in Canada to go. The lack of an indoor is more than compensated for by the dry, above-freezing winter days you'll be able to enjoy. You can avoid the basement suite issue by living above a storefront (as I did during my 5 years on Commercial) or living in one of those slick glass hi-rises downtown. Having a roommate might literally mean having a roommate, so you might want to bring a pal and shop around for a bunk bed. Still, you can live off buck-a-slice pizza, cheap falafel, free meals at the Sikh and Buddhist temples, and a love of skateboarding. Wow, the more I think about it, the more I'd like to move back.
My most frank advice, however, is to leave Canada altogether and settle in SF, LA, Chi, or NYC. Any of those is a much better city with greater opportunities than any of the of the three Canuckistan cities I mentioned. Greater income potential, lower overall cost of living (apartments are pricey in SF and NYC but most other things—from mobile phone plans to groceries to designer clothing to electronics to car insurance to transit passes to tacos to falafels—are cheaper) and just greater cities overall: culturally, climatically (except Chicago), architecturally (except LA), culinary, etc., etc. No U.S. visa? No problem! Just marry an American girl.