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I think sinking an entire fleet borders too much on the impossible side (though undead pirates and voodoo and all that borders on the tolerable edge). Chapter 3 could be well enough and all, but to put a permanent close on it would leave the game less appealing--perhaps Jolly could just declare that he'd have revenge at the end of the mission--after all, his undead would still litter the Caribbean. Chapter 4 could be somewhat well managed involving Davy Jones, but I think it'd be more suited to just escaping the Dutchman. It could be something where Jack tells Davy he'll give him 100 souls, and you're the first (which is where the escape part comes in).
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