Pirates beginning to click

I think my pirate game is finally beginning to click. The game will start when all players will get a card that describes their character's background. Some will be Navy, some former Navy or former privateers, some will be abused merchant sailors, some will be non-abused merchant sailors, some will be slaves. A few will be merchant captains as well. So approximately half will be legitamate sailors, and half will lean towards piracy.

Pirates- form their own "ships" and hunt loot from other pirates or legitamate ships
Legitamate sailors- must transport goods from one location to another and capture pirates

When a pirate and a legitamate group meet each other (or two pirate groups), they can challange each other through some kind of moderated activity.

One example: Kaboom

If the pirates win, they get the loot the team is carrying. If the sailors win, pirates get turned into the authorities (???)

Winner: whichever pirate team has the most loot divided by the number of team members, or whichever legitimate team successfully transfers the most loot.

This could work, now I need to find some more good challenges between two teams. I'm looking at Double Dare challenges, and need to scope out the Come Out & Play site...