I'm of the opinion that I'd need to be competent (by my definitions) before I could even consider being a pirate. I'm pretty sure I could rock a lace-up front corset and all, but could I even walk in those boots? I don't think so! And parrots? Those loud fuckers ... did I ever tell y'all about the time one attacked me and I had to fight it off with a skillet? No? Well, I did, and I've got scars, and...
...yeah. In all seriousness, even if I believed I was competent enough PvPwise (and had the time/ability to do it properly, like being in fleets and on Vent and shit), I'd have to do some hardcore storywork before any of my characters could even consider piracy as a profession1.
Here's where I get around to saying -- Senn, the bits of the backstory you've shown us do seem conducive to someone who'd go pirate for the perceived easy money. If you agree, and you think you'd enjoy it, go for it!
1Even if Vieve and Kyoko were actually having pyjama parties.