I might be able to help you with the insurance requirements. I've found out recently that you can get event insurance if you register as a club with USACycling and it is extremely resonable $2 per person (can be rolled into the registration fee) and $25 for the event. It sounds implausible, but they make it work. That is for a race - it might even be less, considering that it is a fun ride. You do have to register a club with USACycling, but that is fairly simple and only costs $150. I can look up more information on this if you'd like.