Cougar is my SVS Specialist - with maxed cannons and points configured to favor svs.
Kat Five is my treasure hunter.. with the famed Golden Charm and maxed treasure sense - I use her when the guild want to go sailing for plunder and gold.
I have not decided Jag's fate or Fire Tigress.. But I do like the idea of specializing your pirates. I usually make that decision when they are close to mastering, and depending on the luck of their drops.
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