[Aerozord]

if he doesn't view the crew as his nakama then that alone makes him poor first mate material.

Guys can always go with like, Crimson Bandana Pirates and have your flag be the usual skull and cross bones but with skull wearing a red bandana

Old question I forgot to answer. I will not expect you to keep inventory, just a rough idea of how your supplies and money are going so you have to think about it. Occasionally you'll need to restock, though how you do this, actual piracy, purchasing them, hunting, whatever, is up to you. But it will be a good excuse to either do non-plot specific stuff in a town or make unscheduled stops at various islands.