Hey - I'm neither a chick nor looking for roomies, but I think I can help you out some:
September can be a bit of a harsh time to move here, because that is when ~everyone~ moves here, so everyone is looking for jobs, and everyone is looking for a place to live. July and August even are way easier times if you can swing it. Plus the weather is rad then too.
Getting a pad is way harder than a job - a local newspaper called the Pique is the best place to look. It comes out on Fridays, and as soon as it does, landlords start getting calls. You can see the same listings on Thursdays though if you look at the paper's on-line listings: www.piquenewsmagazine.com - its the same stuff as in the paper, but the night before so you can get the jump. I'd suggest showing up with 1st, last and rent cheques in hand, as it is TOTALLY the landlord's market. Dress nice, and if you aren't already, pretend to be responsible. I've been the guy interviewing tentants for the landlord when I was moving out from a place, and it is _stupid_ competitive at times. In the summer like I mention though, way easier. October = almost zero chance unless you want to pay $1500 to share a room (no shit). Don't get too bumed though, its not impossible, just challenging.
Jobs: The mountian hires about 3000 seasonal employees a year in the fall. Depending on the job, they pay ok, and you get a season pass if you are full time. There is also the option for staff housing with them, if you don't mind cramped quarters and shared rooms. They do applications on line: http://www.whistler-blackcomb.com/company/employment and there will be contact information there for staff housing too. If you are intersted, I can give you some names to ask about all of that if you want to call. They hire anyone from lifties to instructors to accountants. Its kinda first come first serve though, so don't sit on it too long.
Lots of other companies hire here as well, some have staff housing, some provide passes, lots of those are hotels. Half decent jobs with them (nights, ok pay) are banquet server positions if you can get one.
There is usually very, very little work here in the fall (October though Christmas). So, you'll want to either come with a wad of cash, or sort out some work that is not dependant on the mountain being open.
My best advice to you is to show up in the summer if you can, get a job doing whatever (serving, retail, anything) and a place to live, so you can get through the fall. When buisiness in town drops off and hours get cut, you'll already have been there, and when others are leaving town for the fall, you'll still be getting paid. When the season starts - at around your Thanksgiving - baddabing, you're set.