The only real way to 'mess up' a pirate would be to hastily apply skill points that cannot be changed in the future. Recommend never applying 'extra' skill points, until you master the particular weapon/skill involved (it will make leveling that weapon easier).
( I apply one to each skill as it becomes available, just to have it, and save all additional points for later)
Keep your weapons levels somewhat balanced, work on leveling them, most recommend leaving the story quest alone (although its often what draws a number of us to the game at first, probably why we all learn the lesson on pirate #1 hehe). Do any weapons and teleport quests as the become available. It will be easier to do the quests when the time comes with a strong pirate with more powerful weapons as well.
As for the guild/vent question, id have to side with Sarah
