[@Sunflower]

Well I don't think I will take on too many major side characters, after all there's a whole crew to rp for as well. However I think I will end up doing at least a couple major side characters, Barley being one of them. I wouldn't mind tying in the woman with Barley somehow especially if you have an idea. I think that would be fun to add that kind of twist to the story.

I could see him stranding them on one of the small floating islands, I think that would be interesting, maybe he steals The Silver Arrow along with the map when he leaves the two stranded and they have to figure out a way to get to him.
If not stranding them on an island maybe he leaves them to die in an old pirates cave on one of the main continents, but basically out in the middle of nowhere.