Well my friends and I have had this debate several times. I think it all depends on whether you would want to be threatened by natural disasters like a storms on the sea or real people like sheriffs and bounty hunters.
Also, since females were not in good positions (no respect, rape, ect) it would be easier to hide my gender as a cowboy than it would being a pirate (smaller living space, crowded).
Wait? Have I been rambling on and on about cowboys and pirates? NEVER MIND!
Pirates are cool in the cool rugged nifty way, but Ninjas were way more hardcore.
Has anyone ever read the
Ultimate Power book / website about ninjas?