No, it doesn't work the way you think. Vail and the insurance company are two different entities.
"Rolling the pass to next season" means Vail won't get to sell you another pass next season.
You filing insurance means Vail gets to keep your money for this season and sell you a new one next season. Yes, the insurance company has to pay out, and they may wish you don't file. But it makes no difference to Vail whether you file or not.
Agree with this. Vail's stance makes 100% sense in this case and this is exactly why they use an insurance company to handle claims like this. There's a lot you can fault Vail for...but this isn't one of them.