Ric Widenor works for the YMCA in Boulder, Colorado, and has a system set up where he collects all the prizes himself, and then he lets shops run their own specialty advanced events, using the YMCA facilities. This way there's no hassle for insurance or skatepark rental, since his events are covered under a relationship between YMCA and the Parks and Rec department of the county. A situation like this is ideal. Look around - there might be opportunities like this in your community just waiting to be discovered.
Waivers are also a good idea - have the skaters sign some sort of waiver saying that the skater is doing this at his or her own risk. If the skater is under 18, you should definitely have the parents sign some form of waiver as well. This has the double effect of protecting your backside and serving as permission for the kid to be there!
