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You would have to argue that his use of your boat was consideration for contract, because without consideration, the contract could be voidable. In other words, your skipper can't be bound to a contract, if they aren't paid.
In the end, the contract is silly, IMO. The bottom line is that the owner is fully responsible for the boat, period. I remember when I first learned that. Hard to swallow, but its the way it works. The point about checking with your insurance carrier is the critical feedback above. I've had times when they added the rider for free and times when they wanted a few hundred dollars. They've always wanted a copy of the deliver skippers certificate.
In the end, the contract is silly, IMO. The bottom line is that the owner is fully responsible for the boat, period. I remember when I first learned that. Hard to swallow, but its the way it works. The point about checking with your insurance carrier is the critical feedback above. I've had times when they added the rider for free and times when they wanted a few hundred dollars. They've always wanted a copy of the deliver skippers certificate.