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Would seem it really comes down to each pirates preference and play style.
Some of what I hear pirates say is easiest, are toughest for me, and some of what others say is toughest, are easiest. I'll stick to my preferences.. hehe
If I were to order them like everyone else.. it usually pans out like this:
Grenades (but not because they are easiest, because I focus on them due to my shear hatred of them), Sailing, Doll, Pistol, Cannons, Cutlass, Daggers, Staff
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