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 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.
Grege has the right idea. Pure I-20 dock, to DAC, (I use a Schiit Bifrost or Bencmark USB DAC1) to preamp or amp.
Get a Bryston BDP-1 digital player. It now has NAS capability so you can play right from the iTunes on your computer if you have Ethernet connection to BDP-1 from router. Even without, if you copy your iTunes onto HDD or thumb drive(s), you will have outstanding SQ and support. For a system like yours, a dock would a massive underperformer.

Neal
But what about those of us who need USB out from the dock? I DO NOT want my computer in my lsitening room, just to listen to Lossless files on my iPhone through my high-end DAC with USB (and no SPDIF) input.