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
I use a Wadia i- transport with battery power supply - pace car - DAC of your choice on one system and a fully modded ASI-TEK wadia i-transport on a second system ...both with excellent results
Fully reclocked Asi -Tek/Wadia i-transport with Acoustic Revive SP/DIF cable into quality DAC (I use Antelope Zodiac Gold). Do though consider using a Mac Mini with Puremusic via USB for even better results.
I dock my iPod classic onto a Peachtree iDac, which can take the raw digital data from the iPod and convert it to analog using an ESS chip. Only a few docks are licensed at this point to take the raw data from the iPod. I store my data as Apple lossless and it sounds great on my home rig. Only drawback is that the iPod can't store hi-rez files - no getting around that.
1. PURE i-20 digital dock + DAC of your choice.
2. The new Luxman dock is very good too.
3. Avoid the Wadia, the quality is subpar for the price charged.
I currently use the Wadia i170 and Simaudio D100 w/ excellent results. I've previously used combination DAC packages by Peachtree, Wadia 151, and Bel Canto C5i w/ equally superb results. Apple lossless playback and you have an ultra convenient way to your music collection.

John