First it's important to know the details of what the insurance plans are NOT.
It is not a guarantee for the whole season, As sib said, most of the insurance plans discount the days used. So once you've broke even in day tickets, the insurance then loses it's value. Often this is done in very few days once the season starts as day tickets are very expensive.
Also these insurance plans are not a cheap cancellation policy. You need to have a qualifying condition to get a claim, you can't just say you decided not to ski this year.
So then what really is covered is just severe medical during the offseason. So what you're betting is you you have a debilitating injury within the next 6months that for your $15 or $20, you get $600.
Hopefully you aren't betting for injury and if it should happen your ski pass maybe the least of your worries and you might not even remember to file your claim.
The traditional thought pattern for insurance is a hedge to provide future money in the case of an unfortunate situations. Say car insurance where if your car is totalled, you need money to repair or buy a new car, or medical insurance where a medical bill needs to be paid for.
If you don't pay the ski rental insurance on rental skis and the skis break, you would be at a loss for an extra $600 by the ski shop which could be something you might not afford.
That scenario to protect against loss is not the case here. For ski pass insurance, If you do break your leg, will getting the $600 ski pass money back be something you really need? No, that is money that is you already spent for "recreation". So while it's a shame you can't ski, you don't really need protection to replace the "recreation" that you lost.
So I view ski pass insurance is just a "bet" and somewhat tempts the gods. Moreover it obviously must be a bad bet with a house edge as the plans must be profitable to the insurance companies otherwise they wouldn't offer it.
I suppose an open scenario where the odds can be in your favor is if you are female and are planning for pregnancy, but unsure if that would happen this summer, because that scenario is under your control and you are planning to some degree.
Edited by raytseng - 8/5/16 at 12:24am