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I'm in the exact same boat as you... there's quite a bit of quests on port royal from the bar maid, lucinda, etc... but they are either really easy (kill 2 skeletons, sink navy ships for rum, etc) or really hard (kill Dregs, etc) I haven't run across any medium level ones.
Keep a lookout for townspeople with gold chests above their heads- they have quests you can do.
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