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Based on the legend of [url=https://en.wikipedia.org/wiki/Libertatia]Libertalia[/url], the general storyline would involve piracy (duh!) and the establishment of a colony of free men and women who would seek refuge from the tyranny of the old monarchies. There would be an accent put on shipboard life, at least initially, survival, as the resources would initially be meager and the island essentially deserted so everything would have to be built from scratch.

Here are a few possible roles I have thought of.

Crew roles:
[list]
[*] Captain: That's me. You're out of luck, you mutinous swine!
[*] Quartermaster: The quartermaster is next in line after the captain in exercising authority over the pirate crew. His authority on the ship takes up where the captain’s leaves off. Whenever the ship is not in chase or battle, the quartermaster makes most of the decisions regarding the day-to-day ship activities. The quartermaster is elected by the crew, and is expected to represent their interests, for which he receives an extra share of the treasure. His main function is to protect the crew against each other by maintaining order, settling squabbles, and distributing food. The quartermaster usually also keeps the account books for the ship. He can punish the crew for disobedience and frequently mediates minor disputes among the crew. The quartermaster also quite often leads any boarding action, being the first to board the Prize ship.
[*]Sailing Master: This is the officer in charge of piloting, navigation, and the actual sailing of the ship. He determines the course and looks after any and all instruments needed to navigate the ship.
[*] Boatswain (said Bos’n): A boatswain’s duty is to supervise the maintenance of the ship and its naval provisions, such as tar, pitch and tallow, spare sails, etc. He must inspect the ship, sails and rigging each day, and report their condition to the quartermaster or captain, as appropriate. The boatswain is also in charge of all deck activities, such as weighing or dropping anchor, and handling of the sails.
[*]Master Gunner: The master gunner is accountable for the ship's guns and ammunition. This includes sifting the gunpowder, to keep it dry and prevent it from separating; making certain that the cannon balls are free of rust, and that all weapons are in good repair. A knowledgeable gunner is essential to the crew's safety and effective use of the ship’s cannons.
[*]Surgeon: The surgeon is responsible for the fitness of the crew, and the treatment of the sick and wounded. As a person with critical skills that are sought after in many places, the surgeon is also often an unwilling recruit on a pirate vessel...
[*]Sailor: The common sailor, who is the foundation of the ship’s operation, needs to know the rigging and the sails. He needs to understand how to maneuver the ship and how to sail under different wind conditions. A good sailor can discern weather patterns, read the stars, and, most importantly, can anticipate the wishes of his commanders. A ship’s crew must work together in careful synchronization to maneuver a large sailing vessel while tacking or wearing the vessel, or while docking or weighing anchor. A capable crew is critical during battle maneuvers, when the exact position of a ship makes all the difference.
[/list]

Eventually on land:

[list]
[*] Tavernkeeper
[*] Governor (yes, the colony's governor would be an elected position)
[*] Perhaps a council of captains, should things go large enough to have more than one crew
[*] Trader / Fence to trade with other colonies and acquire that which cannot be produced on the island
[*] Whatever else: These are critical positions, but I'm sure people can think of interesting people to be part of a pirate crew.
[/list]

I don't want to write too much in one sitting because I'd like this to be as much of a collaborative creation as possible. If you have ideas to propose, please, please do. I have not, for example, determined the type of setting. I'm open to gritty realism (actual nations and maps), high fantasy (bring on the knife-ears), Pirates of the Caribbean style... (If you propose to be Jack Sparrow or Mickey Mouse I guarantee you a quick drop and a sudden stop. *points to the noose dangling from the yardarm*)

Welp? What'll it be? Shall this one sail, or be marooned?