Alright, it might seem a bit cliche, but it's a handy way we can just get to writing instead of dilly-dallying over the details here in OOC. I'm thinking my main guy is a new hire to the crew. Maybe signed up at a posting board (if these pirates are "good-ish"), maybe sent to pick up the crew's trail with a vague series of clues in hopes of getting in (if these pirates are a bit more clandestine). But once he finds them, and gets the tentative "okay", we can hammer out the who's and what's of the job and the world and the story overall organically as he tries to piece together what exactly his new job entails (plus it allows for a lot of character interaction and development, yay!).

And, for the record, this month break is why I wanted to trade emails so long ago :p