My first pirate was before I upgraded. I messed up his skills bad, since I could only put 2 points into each skill, and wound up putting 2 points wherever they would go.
My second pirate, I did the skills much better, but I also did the Black Pearl quest. No big deal, I had fun, but I finished at level 27 or so. He's now 29, and his weapon skills are all around 15ish, except grenades (9) and cannon (22) (what can I say, I like cannons).
Then I created that leprechaun for the
screenshot contest, and since I had to play him a bit to be able to dye his hair green, I kept on playing. He still has the initial "Visit Joshamee Gibbs" in the journal. He just hit 9, and just finished getting his dolly and the Tortuga TP quests. His weapons are all at 6. I think I was significantly higher with the other two when I finished those, all because of the BP quests.
Not sure if I want to keep playing him or go back to the second one. Maybe play the second one until I get word that they fixed the level-triggered quests. It's FUN playing the lower levels when you have a better idea what you're doing.