|Captain Sakhbet "The Sandman"|
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Pirates in the shackles have a good thing going. Anyone that wants to trade with Sargava, Droon, Bloodcove and 2 other Chell colonies have to thread the needle of the Shackles and the open scary open Acadian Ocean. The "free captains" and pirate lords are more than happy to pick off small fish pirates encroaching on their gig. The PC's start as such small fish. At a certain point they become more expensive to kill than use. The offer is they can move goods, offer some legal protection, and so on all things that might risk problems in the north or Inner Sea.
A shift of perspective is needed I think. The AP tells about the 'Freedom loving pirates' but it really is 'Free to do whatever to whomever' more often than not. It is freedom of the moniter-free playground. I remember a Something Positive strip where one guy was going on abotu wanting freedom, so another did a 'stop hitting yourself' routine about how it is the eternal playground, stronger on the weaker deal.
Free captains are supposedly free from being attacked by other free captains and pirate lords. If you are not free captains and you are wondering around the shackles, you are just meat for much higher level pirates.
Consider this, but take it to a more extreme degree. They don't want 'freelancer' pirates gobbling up what they consider to be their loot, they don't want unaligned pirates starting fires they may have to put out or disrespecting them in their own territory. Create a culture where rogue pirates are preyed upon with deliberate intent and greater ferocity than even merchant shipping... let the players know that they'll be running from other pirates and that selling their goods or even putting into Free Captain held ports for supplies without 'getting with the program' could be problematic at best, deadly at worst.
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I know my PC's would just go with it, but why would my team want to be Free Captains? What reason is there for this? If I can get what I want at another grocery store without a membership fee then why would I become a member of Costco?
In my game? If you're not a Free Captain, or flying the flag of a Free Captain, then you're fair game for anyone who can take you. Free Captains take on lesser captains as vassals. The lesser captain is given a battle ensign to fly from the mast identifying them as part of the Free Captain's fleet. It doesn't exactly provide protection, but it does tell any prospective assailant that they're risking the wrath of the Free Captain by challenging that Captain's authority.
Likewise Free Captains issue letters and flags of safe conduct to merchant ships. A merchant ship flying such a flag turns over sizable fee to the Captain (Who turns over a portion to the Hurricane King) and is entitled to the protection of that Captain's fleet - Any ship of the Captain's fleet is obligated to render aid and forbidden from attacking flagged ships.
So the upshot to joining a Free Captain's fleet is protection and having a posse. It's not a sure fire thing, but a ship from a rival Free Captain's fleet will think twice about attacking you for fear of starting a war. Likewise anyone attacking a flagged merchant ship can expect to be hunted diligently.
And if you're enough of a badass to stake your own claim as a Free Captain it gets you vassals, income, prestige, and legitimacy. You're essentially claiming a title of nobility then backing it with force.
Eitherway, back to the "Why would I want to be". It's not so much "Why would you want to be" as "If you expect to make it you're going to be". If you're not a Free Captain, or working for one, you'll be preyed on by them. If you ever become powerful enough to become one you'll be forced into it - It's that or fight their combined fleets because you're becoming a threat. It's really just politics. Free Captains are the nobs of the Shackles. If you're one of them they can keep an eye on you and exert a certain amount of control over your activities. If you're not then you're an outside threat to be eliminated.