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
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.
For the best sound, I would suggest the following.

160GB AppleTV Classic (New or used). Basically an iPOD with a digital output and TV interface.

DAC: Bryston BDA-1 or Pass Lab D1.

You can control the AppleTV using the supplied remote or use the remote app on your iPhone.
If you wont the best sound use only Ipod touch last generation ! I use it with Onkyo NS-D1 digital dock!
Cheaper and better than WADIA and the sound is absolute killer !