One of these days, when I have enough time before a plane flight, I'm going to follow the letter of the rules while showing off (in a non-threatening manner) how easily they can be worked around

You don't even have to work around the list of things you can't carry on board; items on the list get missed all the time. Jeffrey Goldberg of the Atlantic had an article from last year detailing all the things he's managed to sneak onto planes, including pocketknives, matches from hotels in Beirut and Peshawar, cigarette lighters, nail clippers, bottles of Fiji Water, and box cutters. He's even brought two cans' worth of beer through security by wearing a Beerbelly under his clothes and walking it through the metal detector. And this in spite of the fact that he was selected for secondary inspection at the time he was wearing it.

He's also tried forging and printing out his own boarding pass (with help from Bruce Schneier) and getting through security with it, with similar results:

I would try to pass through security with no ID, a fake boarding pass, and an Osama bin Laden T-shirt under my coat. I splashed water on my face to mimic sweat, put on a coat (it was a summer day), hid my driver's license, and approached security with a bogus boarding pass that Schneier had made for me. I told the document checker at security that I had lost my identification but was hoping I would still be able to make my flight. He said I'd have to speak to a supervisor. The supervisor arrived; he looked smart, unfortunately. I was starting to get genuinely nervous, which I hoped would generate incriminating micro-expressions. "I can't find my driver's license," I said. I showed him my fake boarding pass. "I need to get to Washington quickly," I added. He asked me if I had any other identification. I showed him a credit card with my name on it, a library card, and a health-insurance card. "Nothing else?" he asked.

"No," I said.

"You should really travel with a second picture ID, you know."

"Yes, sir," I said.

"All right, you can go," he said, pointing me to the X-ray line. "But let this be a lesson for you."

When you have nothing you have nothing to loose.

Except your extra vowels?

And it's not any more valuable to me than another hard drive, because I don't have any interest in the data on it.

That's only because you haven't seen the size of his porn collection.