you're all good as you don't have a dui or anyone in your party. ski trips are never a guarantee you just pull the trigger and hope. went all the way to france late december and it sucked, went to bc on valentines day last year and it was just o.k. just got to play the game.
Whistler BC has broken the record of most snow ever in a month this november with 169" now and 30 more to fall in the next few days. I will post a link if you want, but i'd say its looking pretty good.
I believe it is not a problem as long as its been 10 years since the end of his probation. if its been 5 years you are eligible for some sort of rehabilitated status but you better get on it if you want to take care of it by February. they let me in 3 years post dui probation w/ prior dui arrest but no conviction but, i think i got lucky. had to pay $200. There's a lot of info on web but its hard to find any one to talk to. good luck.