Also, the examples you give of Zippo vs. St. Dupont (or however the hell I just typed that wrong... cue CC)
or a Bic vs. a Mont Blanc...I can't really get behind either.

Both lighters do the same thing, ultimately. Excluding the diamond encrusted versions, they both comprise basically the same amounts & types of materials. And the pens, well, I never understood the allure of a fancy pen. I've had some shitty pens too, don't get me wrong, but the Bic, although cheap, has always done it's job. Because the cigar experience is subjective (unlike a lighter or a pen) I CAN justify an occasional Padron 80th.

My neighbor has been enjoying cigars with me for the last year or so. He honsestly prefers Padron maduro londres over a PAM corona.

I'm not saying that a cheap short filler cigar is virtually the quality / cost to produce as a high end cigar, just that as you move into "high end" cigars, they are making considerably more of a profit. How much more? I don't know.