I've had my mind made up since Rare announced this adventure; Merrick's one of my favorite characters in the game, and I'm not about to go against him. (The Reapers can keep their worthless rewards. We Shall Sail Together!)
However, I have a couple of questions that the trailer didn't quite answer. If the Reapers are to win, would another outpost open up somewhere in the Shores of Plenty as a replacement? Along those same lines, will pirates who join the Reapers be ostracized by Ramsey and the other Pirate Legends? (i.e. not welcomed back into the company or the Athena's Fortune Hideout).
I feel like this a decision that should have severe consequences no matter which side 'wins.' It is seemingly apparent that if the Reapers win, we lose an outpost. However, it feels like if the Pirate Legends win, it's not necessarily the end of the world for those who chose to side with the Reapers.