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Like everyone else, my first pirate I rushed through the black pearl quest. Every subsequent pirate, I avoided the BP quest until they were at least in their mid 20s.
I found that doing EVERY possible side quest (many of which repeat) was very beneficial, during the level up phases. Boredom quickly sets in, otherwise. Mercenary quests, Bartholemew Watkins quests, shipwright quests, tattoo parlor quests, tailor quests, jewelry store quests, gypsies quests, Black Mack poker quest, blacksmith quest, skeleton infestation quest from Orinda, SvS quests, PR crime wave. By the time all of those are done, my pirate was high enough to do level-up stuff on all weapons without getting blasted.
On my fully-mastered pirate, I still do the mercenary quests and the Black MacK poker quests.
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