Imagine a blow dart which if it connects with another ship (ghost, skeleton, player does not matter) or an enemy NPC/player it unfurls an interactable ghost note attached to the dart.
This note has the terms set out by the player who shot it out which one option out of a pre-selected set which dictates the terms of what the player wants to wager (I want a piece of loot, I want you to alliance with me, I want to sink your ship, I want a million of your gold, I want a rank of your reputation). The opposing player sets the terms of the game to settle the wager.
It only starts if both parties agree (in the case of NPCs, they may randomly choose to accept or decline the wager).
Not sure if the wager should be settled in the open world with some sort of minigame or if the magical powers of the blow dart should transport everyone to a custom map made to undertake the wager.
This tool is good for both PvP and PvE as it intends to promote different social interactions among players and is a way for players doing an hourglass match to end. If there are commendations tied to promote its use, that'll help too.