The one thing you have indicated that could be involved with the sound quality is when you indicate:
"is the wav file encoder for iTunes the issue?"
My question to this is are you ripping your CD to your computer using a WAV lossless file then importing this file into iTunes? While I am no expert on iTunes (don't much care for it personally), I thought when a file was converted and brought into iTunes it became an MP4 (which is compressed).
Perhaps I am off base on this, but I would check and confirm that you are bringing the lossless WAV file into iTunes (if there is any conversion, which I thought there was) using an Applelossless codec versus the standard MP4.
Also, I suspect that the internal DAC is part of the issue, but it sounds like you are already planning on doing something about this.
"is the wav file encoder for iTunes the issue?"
My question to this is are you ripping your CD to your computer using a WAV lossless file then importing this file into iTunes? While I am no expert on iTunes (don't much care for it personally), I thought when a file was converted and brought into iTunes it became an MP4 (which is compressed).
Perhaps I am off base on this, but I would check and confirm that you are bringing the lossless WAV file into iTunes (if there is any conversion, which I thought there was) using an Applelossless codec versus the standard MP4.
Also, I suspect that the internal DAC is part of the issue, but it sounds like you are already planning on doing something about this.