I've been buying a lot of the CD's I've downloaded over the years and replacing the downloads with my high-quality rips. Generally I'll delete the songs from iTunes and the folder I keep them in, and just drag my rip back into iTunes. I noticed my iPod doesn't seem to care that the library has changed (bitrate wise) as it's set to automatically sync my entire library. Is there any way to force it to replace what it has stored with what I've changed if it's just a higher bitrate? I've also noticed my iPod doesn't like to sync when plugged in. I have to reset it (while attached) before the computer recognizes it lately. Otherwise it just sits at the "Do not Disconnect" window.