Ken you need to get off of Boatie's back. He has played nice with you, time to reciprocate
Anyone with any sense at all will contact their insurance to determine the coverage if they are having their boat delivered over Oceans, most likely they will have to purchase additional insurance and send a copy of the delivery Captain's Resume, regardless of whether the Capt carries insurance, however if they do, I would assume your insurance Co would want details.
Bottom line your doing something, anything maybe out of the ordinary, a call to the insurance Co is warrantied, myself I want an
email from them explaining what we talked about on the
phone for my records.
Especially if the boat is your domicile and represents a significant amount of your wealth.
Now if your a Lawyer and can interpret the policy, then maybe you don't need to call, I'm not, so I would call.
Hiring a free lance delivery Captain is no different than hiring a free lance
fiberglass guy, painter or anything else. If you require a million dollar insurance coverage, best stick to the big yards, and pay big yard prices. Nothing at all wrong with that, that is why they are there