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The "Tracking Star" on the map has jumped between quests on me, but not to a place where I didn't have to go for at least one of the quests I am working on.
As for the issue of sinking other ships, I found that when I helped sink a ship with another ship (me on my Frigate, someone else on their ship working together), that I got the drop for the quest. Have you tried getting one of your guildmates to set sail at the same time as you and then both of you take out the ships together?
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