One of the difficulties for me is that I didn't want to rip my collection down into a compressed format. I wanted the original copies to be lossless. I started out doing them as .WAVs and learned that you can't get album art if you do that, since the album art is embedded in the music file itself and .WAVs were never setup for that.
SO, I went back a second time and re-ripped everything as "Apple Lossless", which is fine except for the fact that each song is between 30MB and 35MB!!!
So now I've got a collection of 6000 songs which takes 160GB of space...no matter what I buy, I can't fit the whole collection on an iPod. Honestly, I don't really care about being able to do that anyway...I was just hoping to save a few playlists since in a car, I would typically carry a handful of CDs and only have access to maybe 100 songs.
By some quick calcs, here what I could store on the iPods using my existing Apple Lossless encoding:
Nano 2GB = 57 Songs
Nano 4GB = 114 Songs
iPod 20GB = 571 Songs
iPod 60GB = 1714 Songs
A 4GB Nano would be fine for what I was after, but since it's new I may not have the aftermarket support for some of the cradles and adapters yet...
OR
I was told I can create a separate iTunes library of my entire database using some sort of compressed format, and then load the iPod from that...that way I'd get more songs to fit. Apparently, iTunes doesn't convert "on the fly" from Lossless to a compressed format when moving the songs across to the iPod. (Though I heard that there little "Shuffle" product WILL do that) Hmmmmm????