A couple of behind-the-scenes e-mails reminded me that when you are not the target of Hawaii officialdom, enforcement is mostly determined by whether the waves are surfable.
If you're sailing down to Nawiliwili to haul out for shipping, you might call Larry Conklin and ask him about all this. It may also be an issue if you plan to cruise the islands after the race.
Re insuring the boat, most of us recognize that the SHTP is not an insurable activity. Will, your situation is complicated by your need for liability insurance for the return crew. I'd look for a delivery skipper who isn't as concerned about the insurance situation and may do it solo or with one other person (who also isn't worried about the insurance situation). I know of one who delivered a boat back to SF after its keel fell off. That kind of guy.