"Do they ever fight over who gets to pillage a ship? It seems like with that many pirates in the same place they'd want to sail to the same places."

And then the question is how far they have to go to find the people to take over their ships and their treasures. But they love to sail, that's the whole point, so they probably all went out as far as they could. Jack likes pirates as a concept more than a reality, he'd probably have to reluctantly stop them if they were hurting people around him.

"It was a very small island and hard to find, so they were able to hide since people couldn't easily stumble on it." This is all based on legend, although it has a touch of history, just enough to make a good tale overall. Jack loves history too, he's an eager learner, soaking in what info he can. "I don't know what happened to it when all the pirates were gone. Maybe it's abandoned now."