Unfortunately, your statement "unfortunately maybe no one really does until an accident happens and an insurance company disclaims coverage leading to a court case" is what causes the greatest concern to me. Nothing against lawyers, but you guys are expensive -- and no way to judge the risks considering that I wouldn't know in-advance about the personalities, agility or health of the guests that might win the raffle. If a slip or fall, MOB, collision or equipment failure were to lead to harm; I wouldn't want to be in a court battle with them noting that they advised up front the activity wouldn't be covered.

What I was hoping is that they'd say "since you're not getting paid and you're only giving your time it's still a recreational use, and is covered". The additional stipulation that I be a CG licensed captain is really over the top and easily contested, but I wouldn't want to have to go to court with them at all if there were a claim. I'd want them on my side, which is why we buy insurance.

So from my point of view it's either bring a licensed captain and pay the $500 for the extra coverage, or don't do it.