Quote Originally Posted by LBTC View Post
Hard to say which ones to leave out - we have hundreds of CDs to choose from!!!
Rip them all. If you don't have enough room on your internal hard drive, storage is cheap, and you can locate your default iTunes library on an external drive.

Then create playlist(s) small enough to sync to your iPod. You can include "date last played" as a criterion so songs scroll off your iPod playlist once they've been played. And you can specifically size-limit a playlist and tell iTunes how to sort songs into it.

I've got a large portion of my own library ripped in duplicate at two different bit-rates: hi-res for archival purposes and streaming over the Squeezebox, and lower res for the iPod. But that is a PITA.