I have a large iTunes library most of the music is Apple Lossless format. Most of the time I don't mind that far fewer songs will fit on my iPod because I can re-sync the iPod with different play lists. But sometimes the iPod can't be sync'd for a long time and I'd like to put compressed music on it. My shuffle solves this problem very well because iTunes will compress the music during the sync operation. But this feature is missing on other kinds of iPods. What I'd like to do is maintain a copy of my lossless library in 128K bit per second format then if I want more music I just sync from the compressed library. Questions: What's the best way to initially create the second library? (I have about 14,000 tracks.) What is the best way to maintain two libraries. Rip every new CD twice? The must be a better way.