There are a few things going on here. The first, as has already been suggested, is the law of diminishing returns. To get better genuine performance, that is, lower distortion and more detail retrieval, you sometimes need to spend a disproportionate amount above what you have already spent for the amount of improvement. The second thing is, most differences are just tonal, ie: the frequency response is different. Added to that, a pair of headphones can sound quite different with different equipment for various reasons, mostly tonal again! Why do you think there are so many threads about tube rolling in amps?
However, I think with amps and DACs, one really has to jump up more towards the $1000 mark to notice a significant difference. I've seen a lot of people rotate through cheap gear with little or no improvement.
Next, the price to performance ratio for headphones has been improving considerably as online buying has become prevalent. Take the new full-sized Shure headphones. In measurements they better headphones many times their price. However their frequency response isn't to everyone's tastes. Also, while higher-end gear offers more clarity, a lot of modern music isn't intended to work with high-end gear. Modern pop is highly compressed and very bright which mates well with low-treble high-bass cans like the Beats (or the LCD-2s incidentally!) My musical tastes changed considerably since I first joined Head-Fi. I think if it hadn't I wouldn't have been able to appreciate high-end gear. I still feel I can appreciate music, though not always the same music through my crappy car stereo even or just my portable rig.
However, I think with amps and DACs, one really has to jump up more towards the $1000 mark to notice a significant difference. I've seen a lot of people rotate through cheap gear with little or no improvement.
Next, the price to performance ratio for headphones has been improving considerably as online buying has become prevalent. Take the new full-sized Shure headphones. In measurements they better headphones many times their price. However their frequency response isn't to everyone's tastes. Also, while higher-end gear offers more clarity, a lot of modern music isn't intended to work with high-end gear. Modern pop is highly compressed and very bright which mates well with low-treble high-bass cans like the Beats (or the LCD-2s incidentally!) My musical tastes changed considerably since I first joined Head-Fi. I think if it hadn't I wouldn't have been able to appreciate high-end gear. I still feel I can appreciate music, though not always the same music through my crappy car stereo even or just my portable rig.