I consider Squaw my second home mountain. Great terrain, pretty much anything you want to ski can be skied here. I can ski the steeps or cruise with my wife on the clean forever long groomers and never feel that I am running out of mountain. This mountain is best enjoyed if you are adv. int. or higher.
Nightlife wise I am perfectly content with staying in TC and having my night capper at P&P's. The north shore has some decent places but I like to stay within walking distance to the hotel...Others can take the quick trip round the bay to South T if you have to or the weather lets you (last year I was snowed in! EPIC) Only annoying thing is the Bay fray choking up the pubs.
Not much more to say other than throw Squaw into your yearly rotation and you will never be dissapointed.
BTW, the free lift tickets for the Armed Forces is by far the greatest gig any resort has done that I am aware of. Incredible!