The responses I get are usually along the lines of "well, yeah, it sounds nice, but there's no way I'd ever be spending anywhere close to that on a pair of headphones."
But the thing that baffles me the most:
90% of people I know "care" enough about music to buy a $300 ipod, but don't care enough about how that music sounds to upgrade from stock earbuds.
Exactly. But why the stigma about expensive (or quality) headphones when it comes to price ? I think it's because you can pick headphones up for peanuts and they work, some of them even sound damned good for the trivial amount they cost. Also what of speakers, people don't mind shelling out for those but again not bad ones can be had for as little as £50 for the average person.
It's like banging your head against a brick wall at times with the double judgement going on lol, they're judging you because you spent what you did on headphones and you're judging them because they're spending money to listen on sub par equipment. Or as said here they spent lots of money on an ipod and then butcher the whole thing by listening with crappy equipment and as they say ignorance is a bliss.
Another thing is nobody can get a bead on a headphone, especially a good one, within a few seconds or minutes of listening in a blind test. It takes hours if not days to become accustomed at which point the quality begins to form. It's at that point where attachment begins to formulate. So it's no surprise for people to dismiss good headphones based on either price alone or an extremely brief listen....give them the headphones for a few days to try on their own stuff and watch their tunes change though!