Get a nice, hand-made dock from Ken Ball at Audio Line Out that is terminated with RCA plugs.
You need to rip in Apple Lossless with error correction on and all of the options under Playback off. This is mandatory and gets you most of the way there no matter what else you do.
Then if you want to take it to the max you need to go to ALO and buy a big money cable...
I recommend one that plugs into the USB port on the bottom of the iPod rather then a 3.5mm that plugs into the top
Reason buying that the USB plug is post DAC but pre the op amps and volume control which feed the 3.5mm plug
Note that in this mode, the iPod volume wheel does NOT control the output level of the USB port - this needs to happen downstream in a pre
Please don't take offence, but you are using an incorrect term - that port is not a USB socket. It's the proprietary "Apple dock". Otherwise, you are correct about the mini-plug being after the headphone op amp and volume control. There are only three pins in the Apple dock that are required for audio - Left, Right and Ground. You can rip the rest out - it makes it easier to solder inside.
To your question about downloading from iTunes, if your interest is in getting the best possible sound quality and you have the option of ripping the same music from a CD, yes, it's a bad idea to download from iTunes. All iTunes music is in lossy, compressed format and won't sound as good in a high-resolution system.
On the other hand, the selection in iTunes is huge and for lots of uses the quality is just fine.
do the math - depending on your tastes and how many cds you plan to acquire you might do better buying used on Amazon - and no limitations on how you use the music ever after
Like Metralla I have 2000 cds and nary a one from iTunes.
And yes I had one of Vinnies iPods for awhile. Long gone now but it was lovely while I had it
Thanks for the suggestion to buy used CD's on Amazon. Certainly makes a lot of sense. I will explore this option. Is Amazon one of the better places to look for used music?
iTunes is like buying a candy bar in the check-out aisle of the grocery store. Immediate and convenient, but not very good for you...
I agree that for any kind of critical listening you'd want the highest quality file possible for your music server, CD quality at a minimum and even higher if you can find it.
But, I listen to music in a lot of situations, planes, the gym, in the car, where the difference between a 256kbps mp3 and a lossless file just isn't audible. Being able to download and discover new music conveniently and cheaply is great. I don't get a lot of music from iTunes but have a subscription to emusic.com that I've found to be great for exploring music I might not otherwise ever know about.
I like Amazon as opposed to ebay because I get a lot out of reading the reviews and commentary - very handy as you discover new "families". I also like the samples. And of course I get my cover art there too. Plus you have big brother Amazon behind each deal - in the very rare case of a problem (like 2 in four years) they can put the lean on.
I am sure there are others but this has been a really nice all in one for me and the offering is very broad.