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I think you have a point. Many a pirate wants wild island teleportation, but you wouldn't need your ship as much. However, does that little bit of sailing really matter? I know I sail a LOT more for plundering than to move from island to island, especially since the rides are so short if you head the the closest major island and sail your fastest ship from there. I don't think it would hurt the game, in that way. I think it would hurt it in the way that it just becomes too easy and simple for pirates. My parents always taught me that things you don't want to do builds character. And pirates can always use some character building!
As for your quest, I do like it. It's very similar to the last part of the voodoo staff quest, where you have to defeat an enemy on every island. But your idea is a bit different, with specific enemies and numbers.
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