IPod to home stereo - How to get best sound?


I have a 160 Gb Classic iPod, almost full, with mostly AIFF files, and want to play back through a $50K home stereo.

Should I reload the iPod from ITunes with Apple Lossless?

What docks, D to A converters, optical or rca cables, remotes etc. have you tried and gotten great results with.

I have only used the Apple dock, with Monster connector kit RCA's into my Pass Labs X1.

NEED SUGGESTIONS or suggested sites that will get me there? Do not want to spend more than $2K.
don_c55

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