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Convoys
I haven't fleshed it out, but some sort of convoy that appears at some part of the sea and travels to the other side of the map, like spanish conquistadors returning to Spain laden with gold (timeline probably wrong, but something like that). Always high level with lower level screen around. Something one ship would have trouble with, but several ships attacking together could overcome. Have it sail right past Devil's Anvil to seem inviting. Maybe several flagships as the prize, but other ships around so that if you board without cover, you may come back to a very leaky ship.
Hmm maybe I have fleshed it out!
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