That's the best I could do in my half asleep state. I wouldn't be surprised if it's a wall of nonsensical rambling when I come to read it later, but that's all that's coming out of me for that. 
Just two notes:
1) Tavern keepers will have valuable information about where there is the highest demand for what goods and where there is the most supply (i.e. where you can sell highest and buy lowest) as well as other pieces of information they'd be more than happy to part with if you have a smooth enough tongue or enough gold.
2) Pirates die. People, in general, tend to die. If this RP goes on, your character could die, in combat or of old age (if this goes on long enough.) But as Assallya pointed out to me earlier, a big part of any gang/crew based RP in general is that intimidation and acting big was an important part. A lot of the time it was about who could go the furthest, short of actual combat. Pirates usually preferred their targets to surrender due to intimidation rather than actually overpowering them. So really play on that.

That's my two cents, now go wild.