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My group is in the midst of Raiders of the Fevered Sea, and have stashed a couple of ships throughout the Shackles with an eye to selling them later. They finally decided to move one of the captured ships, and I needed to go look up the mechanics for that, and this is what I found:
"they must ... sail it to Bloodcove or Senghor, the two closest cities in which they can sell a ship"
Really? Why couldn't a ship be sold at one of the ports in the Shackles? Quent is three times the size of Bloodcove - is there some reason why a ship couldn't be sold there? For that matter, it seems like you could potentially sell a ship at almost any reasonably-sized port in the Shackles - you just might not get as much plunder for it.
And then I saw that the same thing was laid out for selling plunder!
"The best options...are...Bloodcove or Senghor...or...Crown's End..."
Again, really? We can't unload plunder - perhaps at a loss - in ports throughout the Shackles? If Quent is 3x the size of Bloodcove, I would expect you would stand a better chance of unloading plunder there at greater profit.
Perhaps there is some reason why Shackles ports are not viable for unloading plunder and ships. How are others playing this?
The AP makes a somewhat artificial decision that the group shouldn't go into the Shackles until they have enough infamy to be taken seriously. I don't enforce this, I just make it clear that they are small fish and have to watch out for being taken by other pirates.
As I recall, the supposition is that Senghor and Bloodcove are the nearest free ports that the great majority of outside merchants are willing to risk visiting in order to purchase local goods and other items "collected" by Shackles - entrepreneurs.
All ports in the Shackles themselves are "Pirate" ports, and shunned by outside merchants lest they lose cargoes, ships and crews to the local predators.
The Plunder system prices are based on the free ports, as that's where the folks with gold to spend come to buy. I suppose there is no real reason why some plunder or captured ships couldn't be sold inside the Shackles to other pirate captains as a side deal, but I wouldn't expect to get anywhere near the standard values in gold. Pirates are notorious for spending their loot as fast as they acquire it, or burying it on some island somewhere (and then getting drunk and losing the map ;D ) so they're not likely to have the same sort of ready cash as a Senghor or Bloodcove buyer might have.
There are merchants that travel into the Shackles to provide supplies and materials that pirates might need (Quent is a prime location for this as is Port Peril, IIRC) but there you are talking more about people with things to sell to pirates, not buy from them.
My take on it, anyway. No reason why others couldn't handle things differently in their campaigns.
Pirates don't pay. They take. No secret Bonefist-issued "Letter of Marque"? Good luck.
At least, that's the impression I get. Which is later mostly contradicted by Part 3 and the whole Port Peril write up. Still, I guess the assumption is most of the traders in the Shackles aren't lvl 3 minnows waiting to be gobbled up.
Part 3 is for when the PCs have gathered enough clout to go up to the Hurricane King to prove their mettle "safely", then those Shackles ports would open up to them. (They were open all along but it was a matter of likelihood of actually getting there unmolested.)
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I ended up creating a "pecking order" type mentality in the shackles based upon reputation.
Council Pirates.
Free Captains.
Other established pirates.
Newbies.
PCs are always free to go to a port in the shackles, but without a dangerous rep, they are anyone's meat. This gives incentive to climb the ranks. If players still insist on going, use some role playing in port to bring it up- merchants treat them badly, bartenders ignore them, whores laugh at them, other pirates (Gortus Svard!) pick fights, etc.
Also, it is noted (somewhere...) that most free captains are "sponsored" by other free captains. Going it on your lonesome is supposed to be difficult and dangerous... and fun for evil GMs everywhere.