Advanced Skills
At prestige level 1, cabin boys choose one of three classes - Hunter, Sailor, Craftsman or Scientist. At prestige level 2, crew members choose a specific career path available to their class which locks them into a specific set of three skills, which are then unlocked as they level up. Skills are listed below. Skills in italics add a special die face in combat. Those with two stars ** unlock the ability to invest in selected ship technology upgrades which grants access to purchase different vessels. Those underlined are focused on the creation and use of safe docks. Other skills offer passive benefits, immunities, economic bonuses or buffs of various kinds.
Hiring crew
The tips screen suggests there is a variety of ways of hiring crew from port, but the only one I've found is visiting the pub. You can hire cabin boys or someone with a professional skill; sailors, hunters, craftsmen or men of science. Each professional has a level (1-10) and you can hire up to your prestige rating in total class levels. Initially that is 4. The higher the rating of the pub, the higher the maximum level of professionals available. Firing a crew member costs you one prestige, but it is sometimes necessary to make space for someone better or with a skill that has become important. If you can earn prestige quickly enough, you can hire level 10 crew that can make surviving battles a lot easier.
Rolling dice and probability
A cabin boy has 33% chance to hit, which goes up to 56% with a re-roll. A hunter has 50% chance, which goes up to 75% with a re-roll, and 87.5% with two re-rolls.
So, for an expected outcome of one hit per boat, you would need three cabin boys, two cabin boys and a craftsman, or two hunters. For a greater chance than that, try two hunters and a craftsman or three hunters (expected 150%).
As your captain, uniquely, has the ability to take levels and skills in each class, he can be ultimately flexible in a fight, albeit game over if he falls. It's easier to hire level 10 hunters than it is to build your Captain to level 10, so I suggest starting him with Sailor and Scientist to begin with (using the Smart trait.) Use the re-rolls by default to maximise offense and swap to healing when necessary. Getting him the Whaler Man and Field Medic skills eventually will give him excellent passive team skills during fights.
Or you might be better off leaving the heavy lifting to the crew for the most part. Your captain does not get morale from killing enemies - whereas your crew does.
Advanced Skills...