I see that when you have a $100 pair, that the headphones aren't forced to do anything and they take on their own personality. All the flaws, imperfections and problems just make the problems come out better. Like Treble on a Grado
But then as you rank up in price, the makers try to cover all the bases all at once and make headphones that are tweaked over and over again and force them to make certain sounds. This would give you better overall sound, but it's like castrating a bull. The meat will be better, but then the bull is only good for meat.
I also see it as a personal preference. I have three major headphones that cover highs, mids and lows so I can evaluate anything I wish. And then they are all under $100. But I can move up and start buying better headphones. It would give me better overall sound, but then nothing "special" to the headphones.
And this is what we differ from "Audiophile" and "Pro Audio User".
An Audiophile is looking for the greatest and best he can find.
A Pro Audio Listener is looking for a product to work the best as possible.
I'm an Audiophile that likes Pro Audio. I like my Grados, but then also love my Fostex