Touché.
I didn't take Apple's ad campaign into consideration. However, the public at large does seem to believe that Mac users are elitists, but I say not true. I am someone who values my own time and money.
Well, the cool/elitist factor has been inadvertently perpetuated by all those Mac vs. PC commercials. The original plan was probably to have PC guy be creepy and unpleasant and Mac being just a relaxed, nice, no-nonsense guy. But most viewers probably ended up rooting for PC, because Justin Long comes off as an arrogant jerk while John Hodgman comes off as adorably helpless. This left an open goal for Microsoft who eventually stepped in and said "Heck yeah, I'm a PC... we're all PC... so?"
Apple never called themselves cool. And they aren't. Jonny Ive is kind of cool, and Steve Jobs is certainly cooler than Bill Gates (the bar is pretty low), but really, they're all just dorks. And the audience at Apple's Keynotes are always a bunch of dorks too, they look a lot more like John Hodgman than Justin Long.
It's really those commercials, and the fact that the Mac has a long history of being used in design, video and music where being cool is a must, plus the pricing model that automatically excludes everyone who can't afford to be cool... oh, and the user base. It's a lot better now, actually, but back when the user base was smaller and basically made up entirely of devotees, they were horrible and scared armies of potential buyers away from Apple. Some of these clowns are still around, yapping about "malware" and other increasingly anachronistic anti-PC arguments, but... it's getting better.
I'm not sure how Apple could rid themselves of the coolness blessing/curse, though, and if they even want to... I guess they tell themselves that it's all about envy, and that envy is just another form of flattery, but seriously -- envy is just pure hate and nothing positive will ever come of it for the target of the envy.