Thanks for the insurance info. At one carrier I was quoted $430 for 2 sleds with $500 deductible. My original rationale was based on if a sled was damaged, between paying the deductible and insurance during the year you're actually paying out 10% of one sled value each year. Granted, that is a scenario with a wreck and isn't as much as the full damage payment but if typical damage is more like $1000-3000 then it may be worth gambling with no insurance saving the money for repairs or a new sled. That is why I asked the original question about how hard it is to total. It sounds like high dollar damage is too common though, so probably not worth the gamble.
Also, I consider it somewhat of a health insurance policy to not have insurance on the sled because then I won't be driving it in some careless way that might hurt me.