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I've always seen the Black Pearl boss battle as easier with smaller crews (like driver and 2, maybe 3 gunners). As Tib said, it used to be more a challenge for majority of the Caribbean.
One thing that has made it easier is the increase in skills in the past few years (lv cap increase for notoriety and weapons: cannon and sailing mainly, and the introduction to sailing items: rams, charts, globes.)
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