Let shipwrights at outposts repair boats for a price. Repair would set all level holes to 0, remove mast cracks, set capstan and helm back to normal, and refresh the boats paint.
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Players should also be able to change types of boats with the shipwrights. They would now be able to start a session with a sloop and upon learning more friends are getting on, upgrade or downgrade to a fitting boat size.
Resources in barrels should be transferred to the new boat but not anything on deck, such as treasure or crates.