Took the family out to W-B and Vancouver last X'mas for the first time. Here are my $0.02:
Agree with whomever said to avoid a stop over flight inside Canada. We connected through Toronto to save some $ and almost missed our return flight due to delays. Having to pick up your luggage and go through US customs in the connecting city is a huge PITA.
Depending on your trip you can avoid car rental. It's a 2 hour shuttle from the airport to W-B and if you stay within W-B you don't need a car. Parking your rental car can get pricey. If you stay in the pedestrian village you don't even need to take a bus. Pretty much everything you need can be bought in the village (there are 2 supermarkets). If you go to Vancouver, you can get around via public transport or taxis.
It's most expensive to stay in Whistler Village. It's slightly less expensive and just as convenient walking to stay in the Village North. We stayed at the Delta which is just over the pedestrian bridge which connects the two areas.
You can rent a variety of gear from W-B and if you do it's complimentary overnight storage near the lifts. Otherwise you can pay for storage.
If you want ski demos or boots or whatever check out Fanatyk Co in the Village. They carry Head and Kastle skis and Fischer vacuum fit system and lots of brands.
That's all I can remember for now.