Assuming you are using the DAC in your Headroom Balanced Max Headphone Amp with The Alps RK-50 potentiometer, it should be pretty substantial.
Bypassing the headphone output of the iPod and using the the line out dock outputs is the first step in better sound from an ipod. Bypassing the internal iPod dac is the next step. Using Wav or Lossless compression is next in line.
There is only so much circuitry that can be stuffed in an iPod. Using it primarily as a storage and transmit device and letting other more powerful gear do all the work will yield as good as CD results.
The iTransport is well worth it's meager price tag. I have new for $379 shipped. Or a Mint Demo for $330 shipped.
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