We recently started a sailboat rental program at our club on Lake Carlyle near St. Louis. We give a short written test to people to verify their ability. We rent for 4 or 8 hours. We rent a Hobie Wave, Some Hunter 18, Flying Scot, or San Juan 21. The harbor master handles the rentals. Unless you have an onsite person to administer the program it would be impossible. We mostly rent the Hunter and the San Juan 21 unfortunately the Wave doesn't get rented too much. Before this program there was no way to rent a boat affordably anywhere. Our insurance is through a US Sailing Program. Rentals aren't cheap but you do have to cover the overhead.