Man, I *hear* you 100%. I think for the money you can get a better sounding pair of headphones, I'm not sure about headsets. They just released the "IE2" series of headphones and headsets and I can't comment on them because I've only used the version that's been out since 2007 (the first zebra striped ones).
I recently broke my headphones and went with the bose headset, even though I knew at the price range I'd be able to get a better sounding headphone, but here's why (for me):
The comfort, the in ear headphones/headset are by far the most comfortable anything I've ever put in my ear. I have 3 hours total commuting time per day by train and listen at my desk almost all day long.. which leads me to my second point. I need to be able to hear what's around me, I ride the subway in nyc everyday so this is just a good idea for safety and train announcements, as well even at decent volume I can still hear the phone ring or someone call my name. The bose set is not noise cancelling. Overall I think the comfort, the fact that I can still hear some environment noises and the sound quality - which to me gets better with less background noise - was the perfect combo of what I needed.