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It's either totally random, or it's about cycling through the loot. I got the general idea from the Pirates Online Wiki. Basically, if you choose a server and you're, for example, getting a skull chest every ten Darkhart kills, try switching server. A theory for getting loot is that other players may have cycled through the loot stages in each server, then left and you can harvest their loot. It's possible. Might as well try.
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