Here is my experience with the whole thing.

I ended up buying a couple of Fido SIM cards off eBay. The day before I got into Canada I tried to activate them online and the Fido web site was down. It seems to do that a lot (the activation site I mean). Eventually I was able to activate one card and put $10 on it. I used an American credit card which went through with me putting out hotel's address but apparently that is hit or miss. Ideally you need a Canadian card to activate. Once I got the $10 on it and chose the prepaid plan of my choice I was able to make calls. However the main reason I wanted it was for data (e.g. To check maps). The data never really worked until eventually I figured out I had to change the APN settings to ones I found on some forum I ended up on through google. Once I changed the settings I was able to connect to the default fido page and purchase a 250mb data plan for about $8, which they deducted from my card.

Apparently another easier option to get money on a card is to buy one in Canada. I wasn't able to find one easily in Whistler but didn't really look too hard or ask around.