Money...

How exactly are we supposed to make money, besides looting the corpses of others? Is there a job system of some kind where you do work to get cash?

Aye, there needs to be some way. Can't live off events alone. Need to do like ship raiding missions or something. Maybe raiding different spots, giving different rewards. Maybe make islands to be captured to over time money supply.
Just some random suggestions.

Great question, and one that will be addressed soon.

The plan is to introduce mini-events that occur on each island, which players can undertake to obtain beli. You can then attack other players for their beli, if you're an evil character. I will also be making raidable towns with preset amounts of beli, again, for both good and evil characters (pirates in OP are morally ambiguous, but there will be a brief synopsis of the island's leader to aid you in your decision).

So it will be done in events basically. Not large scale ones, but theoretically even these can go in scale if multiple screws take them at once.

I still believe having like smaller ways, with less beli maybe, raiding ships would be a good idea.

A list of events that can be cycled over, and can be turned into large ones if multiple people do it, yes. Not massive ones that rely on staff to run them from the start.

Raiding ships would be on the list.

Great. I believe that would solve this little problem. <3