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If you're connecting to the headphone output of the iPod the digital signal has already gone through the DAC and amplifier inside the iPod and the sound is never going to be any better than those two ultra-miniaturized, inexpensive chips produce. You can bypass the amp by taking the signal from the dock connector rather than the headphone jack but you're still going through the DAC in the iPod.
The point of having an iPod is to have relatively inexpensive access to music in situations where you wouldn't otherwise, not to try to duplicate the sound of a home audio system.
If you're connecting to the headphone output of the iPod the digital signal has already gone through the DAC and amplifier inside the iPod and the sound is never going to be any better than those two ultra-miniaturized, inexpensive chips produce. You can bypass the amp by taking the signal from the dock connector rather than the headphone jack but you're still going through the DAC in the iPod.
The point of having an iPod is to have relatively inexpensive access to music in situations where you wouldn't otherwise, not to try to duplicate the sound of a home audio system.