Ive just heard really good things about Whistler and Jackson so I wanted to head to one of those mountains first. Maybe I will look into those other mountains also. I hear Jackson has some hardcore riding but lacks the nightlife and that Whistler has some pretty good riding but the best nightlife.
Well J-Hole is arguably(or not) the most "extreme" mainstream resort in north america and Whistler is the largest.
I'd have to agree that I'd start out smaller\easier which will be more enjoyable and not as overwhelming......shit some of my favorite places to ride are the smaller more out of the way places.
Regardless of what you choose you'll have a blast!