Now, from a consequentialist point of view, Option Two makes the most sense. You could certainly reach more people overall via that route!

But Michael leans more deontological and abandoning his original group would absolutely never sit well with him, so Option One is the clear winner! Pirates seem to have it a lot rougher than all those rich folks back in town anyhow.

ETA: While we're at it, do any of these sad stories involve Ferryn or the current state of like, pirate culture?