The generation of loot bugs me a bit. It would have been nice to have an island that had a sugar plantation on it, another one with a mine for ore, etc. to have somewhere in-game to explain where stuff comes from. However, implementing such just for cosmetic consistency would be difficult with little payoff outside of emersion.
A better explanation and possible world event/merchant mission would be a series of merchant's vessels flying an escort flag that works similar to the alliance flag. The ships arrive through one portal and travel across the sea thieves to another portal. The in-game explanation is that the sea of thieves is a risky shortcut. Players could attack this ship to get the loot or accept the escort mission via their own flag box to sail along with it to protect it. Occasional skelly ships would spawn to attack, prioritizing escort players. The reward is straight gold and rep based on how long you stayed within 1 square of the ship. You have to be with the ship for over 75% of the voyage for it to count for commendations.
Attacking ships would get loot once the ship sinks and commendations. With extra commendations for sinking the escort player ships. Separate accommodations for sloops, brig, and galley.
