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I had a USAA for my 23 foot Chaparral for years. I don't think you should sweat Progressive since they are subcontracting through USAA, therefore you should expect the same service as you would as if it was USAA.
What type of boat?
Many of the people I know who have oceangoing powerboats and sailboats don't bother with insurance, because insurance for the international craft is hefty, and not really worth the cost in the long run, if you're the kind of person that can afford the boat in the first place.
Then again, the same people swear by their boaters insurance on their lake and rivergoing boats.