I haven't had time to look at this since first posting, but should tonight or tomorrow. If it is still open, I'd take a boatswain, however it is spelled. If not, a carpenter.
Congrats, Nomad. Looking forward to your character concept. Azazel, welcome to the game. I like the concept of Simple Jack as well. For the sake of assigning a role in board the Sun Dog, he'd be a boatswain as well. Though, other options for duties are possible as indicated in the PM. I've put the stamp of approvalo on Keeper's sailing master and Hammer's Master Gunner as well.