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
Like so many others I have a Wadia 170 dock going into my Audio Research gear.
All my files on my iPod at in wav form which I found is by far the best format without using a lot of memory.
As far as cabling goes, I am using all Nordost cables along with Kimber digital cable( tried lessor cables but wound up spending around a grand on the digital cable).
My gear is ARC ref3, transport and dac, d400mkii, into Thiels.
Final note is that I am going change my dac to the dac8.
istreamer is simple and no need for preamp. not sure of all the different ways to connect, but mine goes direct to an active crossover.