Haha. wow. Good thing I found out that flying a jolly roger off the shrouds of my 25' Tanzer would cement me as a supporter of not only rape, murder, and theft, but also junk bonds and felonious corporate accounting! Thanks. I assumed that the fact that several US military units past and present (four squadrons of the 90th Bombardment Group of the Fifth Air Force in WWII, several USN Fighter Squadrons, including the current VFA-103, the VF-84, the VF-17, etc.) as well as the entire Royal Navy Submarine Service have adopted as their emblem would have made it apparent that the jolly roger no longer stands explicitly for rape and murder but rather for bravado tinged with lawlessness. Somebody better write all those jet pilots and perhaps the Queen of England and let them know exactly what they're getting themselves into.
I would argue that the historical connotations of the flag have been overruled by more recent usage in military and popular culture. Connotations change. The swastika was a Hindu symbol for prosperity, welfare, and luck. If you were to fly it today, people would associate it with the more recent, popularly understood use of the symbol (The Third Reich) rather than the meaning assigned to it centuries beforehand.
As to the hypothetical aspersions on my character and the assertions that I'd be seen as a 'drunk hillbilly' (by the way, you might want to double-check your epithets - hillbillies live in rural and mountainous areas and have not been spotted in boats larger than 8'), I can probably live with the occasional disapproving glance from hypersensitive yachtsmen. You'll forgive me if I don't deem it necessary to defend my reputation to you. I hope the Coast Guard and any naval vessels I encounter will hold their fire, choosing to capture rather than kill the four or five teenagers aboard the 25' bermuda rigged sloop.
Thanks for the input on black hulls/other fun accoutrement. The plank definitely seems do-able and within my limited carpentry skills. My boat is in RI so it sounds like the black hull might be ok. I might go with a dark blue or green just in case. Cannons look like fun but I might stop short of exploding munitions and stick to a mounted water balloon launcher of some sort. Thanks to whomever suggested getting another set of standing rigging - I was a little worried about messing up mine. Special credit to whoever took the painstaking time to type up 3 paragraphs in pirate speech.
Cheers. And to all of you naysayers - beware, there's a water balloon with your name on it.