I haven't been to Hawaii yet, but I have been to Whistler many times. We always flew into Vancouver and took a limo (I think they also pick up from Seattle). The drive from there was around 3 hours, but if you have any kind of snow storm it added another hour to the trip. We really love Whistler but haven't been back in quite a while due to the Olympics and the drop of the dollar. The skiing is incredible and you won't find anything else like it in North America. The village is fantastic with many fine restaurants, bars and entertainment. We would always rent a condo through an owner (we used alluradirect.com, but I'm sure there are many condos listed on the other owner sites.) and we would always stay in the village as you could walk to everything or take a quick bus ride to the lifts. They have many great shops that you can rent skis/boards from if you didn't want to bring your own (if you were flying to Hawaii right after.)
Just remember that the travel time to and from Whistler will cost you a day each. So skiing for 2-3 days would be a 4-5 day trip in total. We would always stay 9-10 days. If you have the time and can afford it, go for it! You only live once.