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We may be overthinking this...
To effectively have a fair trading system, there must be a neutral third party. My thought is that an NPC (Like a Peddler, or a Pawn Broker) would act like a bank - holding your item and then posting the price YOU set. If the item sells, you either get the money instantly OR you have to go back to the Broker to get it - minus a small commission fee (after all they are business folk).
The Black Market concept assumes that you're selling illegal items. But, if you're a pirate selling ANY stolen wears - it's illegal. Granted that they could ADD contraband for instance. Like some items not allowed on one island but okay on another. If that were the case, then you could only transport them via ship and have to get around blockades or inspections as written before here. That's where we may be exceeding the game's limitations.
I would be happy with the Pawn Broker or Trader idea. However, this further gets complicated that a Broker would then have a sizable shopping list as pirates try to unload their extra Famed items and it would turn into a bidding war. Again, probably beyond the game's realm.
My own idea I posted sometime back is a Trader who only holds the item until the other party gives their money then the exchange is made - likely thru a code. This would also mean you could give friends a nice item for merely a single gold as a gift, etc. But only the parties doing the trade would know the item and price. Its a bit dumbed down but doable.
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