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A high quality pair of IEMs would completely blow away the KSC75s or Portapros and many other lower-priced supra or circumaural headphones. And they certainly are not the best headphones under $300, I'll tell you that right now. Perhaps under $50, maybe. That's not to say that the KSC75's and Portapros are bad, because they certainly aren't, and they're definitely better than the stock iBuds at any rate, which I agree should be replaced immediately.
Anyway, my definition of "iPod accessory" is probably a little different than most people's. I recommend getting a line out cable and a good amplifier, perhaps something from HeadRoom or Ray Samuels. Then get a nice pair of in-ear monitors to top it all off.
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No matter how you pimp up your system, the music is still compressed file, hence it still has limit in term of level. And since Ipod can not play FLAC, I don't think getting an amp worths that much.
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