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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.
 

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Sometimes the technical will take too long to engage in and is pointless.

The practical, even within the law, is what really matters. In the delivery business, the owner assumes the risk to their boat. It's just the way it actually works, in real life.

We can spend the afternoon on exceptions for gross negligence, etc, but it isn't the norm.

Also mentioned above was the idea of lending your boat to a friend. That being the case, I would also say the same as if you were lending money. Do not do it, unless you have no intentions of getting it back and are good with that.
 
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