One idea that cropped up very early on when brainstorming was the possibility of Louis being rather merciful for a privateer of the age. Instead of outright sinking ships he might harass British ships to get on the nerve of his crush the Commodore ... by giving the crewmen makeovers of the French assortment. Naturally a barber doesn't work for free; he'd take off with their cargo by means of "compensation", but as far as he's concerned "Everyone came out alright!"
This was also the first comic I drew that introduced the possibility of the Commodore having a rather hopeless ensign. It was also a chance to explore Jame's blue, stylized uniform side-by-side with the standard red; he stands out more as an authority figure, which was the desired effect.
I just found your gallery and am sad I haven't been following sooner. This brought tears to my eyes from laughter. xD I think I'm going to enjoy reading more about Louis and the Commodore.