Was thinking that if I was headed up to Alaska, etc where bad weather is the rule, not the exception, that purchasing some kind of weather insurance wouldn’t be a bad idea. I know that WeatherBill.com sells e.g. call options on CDD, HDD, rainfall indices.

The cost wouldn’t be too much, but it would be tied to the observed weather a specific weather station. So if it’s nice in Talkeetna but dumping at Mt Huntington this wouldn’t necessarily pay off perfectly. But the basic idea is that if your climbing trip sucks because of weather you can recover some of your expense (unfortunately not the time, though).
-Scotty