Just saw that this thread made the table of contents, so I will add onto it.
We went to Whistler/Blackcomb to ski in January 2010. Stayed 6 days/7 nights.
We got in a day early and stayed in Vancouver at a hotel off of Broadway. We only did this because we got in really late and wanted to make the trek to Whistler during the daylight hours.
Customs was a breeze at the airport, rental car was easy as well. (A little bit of a trek through a couple of parking garages to get to the rental car place, but it was fine.)
I did get lost leaving the airport because of my stupidity. I would've appreciated a little more signage, but it's my responsibility not to get lost, not theirs to guide me to my exact destination. Great roads though and very clean place.
On the drive up (which took about 2 hours), there is no need to snow chains or 4wd in our experience. They do a good job keeping the roads clear. The base was about 130" when we went although it was a hair warmer than normal (or so I was told) with the average morning temps being about 30/27/24 (base/mid/peak), getting up to probably 35/32/28 midday and then falling to about 28/24/21 at night. (All of those are in degrees Fahrenheit.)
We stayed at the Aspens, a ski-in, ski-out in the upper village. This map is very helpful:
http://www.lechamoiswhistlerhotel.com/maps/whistler-map-large.jpg Anything above the parking lots in the middle of that map is considered upper village- or, that was my understanding at least.
From the Aspens, we walked down the ski slope, through the fitzsimmons trail, and then into the village. I'd say it was a 10 minute walk or so. It was not as bad as I thought. There is also a bus that runs.
If it were me, I'd stay within walking distance of the village because you'll likely be there every night- that's where the restaurants are, where the apres is, etc. But, I liked having a ski-in/ski-out, so our location was ideal to me.
Restaurants: We ate out every night, dining at Citta's twice, Old Spaghetti Factory once, Three Below, and Earl's twice.
Citta's had some of the best pizza I've ever had in my life. Good serving sizes- we left with a decent sized doggie bag both times. The restaurant is a bar downstairs and a restaurant upstairs. It's a no big deal place, so attire is super casual, which was nice after a long day of skiing. Food was mostly diner type- burgers, pizza, pastas. We had the pizza both times and some onion rings. Holy cow that was good eats.
Earl's was probably my second favorite place. Very good burgers and great fettuccine alfredo. Didn't have anything else other than beer, so can't comment.
Three Below was actually good as well. It's in the basement of the movie theater building. Had a grilled chicken dish. I'd recommend it, but it's not one that you just have to try.
I looked forward to Old Spaghetti Factory the most and while it was good and was always packed, I was pretty disappointed overall. Again, it wasn't bad and I'd eat there again, but both my wife and I agreed that we've had much better italian at a small fraction of the price.
Onto prices- everything is expensive here. Everything. (Or it seemed expensive to me.) Our normal meal out would be about $50-60 with no alcohol and limited (or no) appetizers. It was not uncommon to spend $15-20pp on the main course and then throw in tip and tax.
Since we were at a ski-in/ski-out, we ate lunch at the condo every day. I don't regret doing that but I do regret buying all of our groceries from the market there at Whistler. I'd compare their market to a small brookshires- quality stuff, yes, but ridiculously overpriced. My wife paid $5 USD for a small box of poptarts. A half pound of no-name mild cheddar (sliced at the deli) was about $10/lb. It was just really expensive.
What I'd recommend you do in hindsight is stop in Squamish- a town about 40 minutes south of Whistler that you'll drive through on your way up. They have a Walmart there right off the road you'll be on. I'd buy all my non-refrigerated groceries there and then only buy the things that need to stay cold up in Whistler.
I can elaborate more on the mountain, but what do I say? It's enormous. I've skied Vail and thought it was big. Compared to Whistler, it's small potatoes. I'd say it's a bit more difficult than CO skiing. Some of the blues at Whistler would probably be blacks some places and some of the greens might be blues some places, but there is plenty of room for beginners as well, so don't steer away if someone in your party hasn't skiied before.
The mountain is weird in that it's got a vertical rise of about 5000'. For comparison sake, Breckenridge only has about a 3000' rise I believe. Vail only has a rise of about 3500'. Jackson Hole is 4000'. In fact, Blackcomb has more vertical rise than all but one other mountain in North America. The vertical rise is not so strange but the base elevation is because it's only about 2200' above sea level.
So, what you end up with, is distinctive climate zones at the base, mid-mountain, and peak. When we went, it was not uncommon for it to be raining and soft at the base, be absolutely a whiteout at midmountain, and then be above the clouds and much more clear at the peak. Just strange to go through all of that compared to CO where you start off way up there.
Anyways, great runs, great grooming- awesome skiing mountain as advertised. Skiing was expensive though as we paid about $350pp (I think) for a 4/5 pass (ski 4 times in 5 days). There are a few places online where you can save on this and I'd definitely check it out ahead of time.
I own boots but rented skis. My wife rented both. Rentals were about 20% more than in CO across the board. We used Spicy Sports for our rentals only to find out (after we had rented) that we had a ski shop in the bottom of our condo complex. Equipment was good, I'd recommend them.
Let's see- what else do you want to know? Best ski mountain ever. EVER! Great town, great eats, great people. Costly, but it is what it is.
We used VRBO for our rental. Highly recommend using that site. We've had zero complaints.