Disclaimer: I've only done the first S&S adventure path so far.
Obviously the core motivation for a pirate is to acquire gold. the way they choose to accomplish this task is by raiding ships or towns. Pirates are also very prideful and desire to be the best at their "jobs."
Goal/adventure:
Drinking in a pub with a fellow pirate crew, the crew begins to argue about which capitan is the best. A challenge is made by the NPC capitan whoever can sack a town and return the most amount of treasure by the end of a month is the better capitan.
Reward:
Loser has to paint "Bested by <Capitan Name> on the bow of their ship for one year.
