Is that so hard?

I have an iPod. It stores 20Gb of music. I also have about 80Gb of music on my hard drive. All I want is a way to put certain select music on the iPod, and then fill the rest with random music selected from that hard drive. Ok, as an added complication, the hard drive lives on a Linux box, and is NFS mounted on the Mac that drives the iPod. That shouldn’t matter, should it? It’s a fast network link (100Mbps) and goes through a switch instead of a hub.
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