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
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
I have the Wadia i170 and PS Audio DL3 with level 3 mods in one system and the Pure i20 with Havana DAC in the other. Both sound very good and when switching them between systems I cannot here a difference, even thou there is a substantial difference in price. Both of them have remotes which work fine. The original Wadia i170 only has coax out and not optical which could limit additional device connectivity options down the road.