Subject to Bennington Dealer interest or not, some manufactures have found "Regattas" to be very effective. A "Regatta" can be structured to focus on any cause or level of society. Or, it may be closed to members and/or conditions only. A "Regatta" may be structured as the umbrella for multiple short term/long term objectives.
The objective of any similar water event is to create a further purpose for the boat/investment. Whereas a family may be involved, there may be "Hot-Dogs and chips" on the beach. Or, a Poker Run/Bennington Regatta at Lake Of The Ozarks during the Offshore Boat Shoot Out, may interest others, etc,etc.
Looking at your event calender, scheduling doesn't seem to be a problem.
IMHO, Liability insurance is mandatory, but affordable.