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I've done the EITC ship sinking part of the Cutlass quest about 3 times now. I solo'ed my own quest on a long. clockwise, multi-stop tour of the Caribbean. I knocked off the same spawn a couple times in a row occasionally, but for the most part I never covered the same ground twice.
I sailed someone else through most of it as a mix between general sail, the EITC Ships, and the Skeleton ships from the doll quest; however, we did work the respawns. The third run through was just a brutalization of respawn points.
I did find it gave me credit more often when I was tracking the EITC ship sinking quests; but, so far as I know, no one that has sailed on my ship has received credit for each ship they sank. There were always some non-credited sinkings, even when the voyage was completely focused just on the EITC ship sinking part of the Cutlass quest.
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