How do I fill a 40GB iPod with random subset of a larger music library?

I have more songs than will fit on my 40GB ipod. I would like to have a random subset of my library uploaded to fill my ipod. And then next time, I want to replace all the songs on my ipod with another random subset of my library. I believe there is a way to do this with smaller ipods. Can I do this with my 40GB model?
Thanks.

You can have Itunes make a smart playlist that randomly selects about 32 GB worth of music onto a playlist, and make that playlist automatically update to your Ipod.
I would then add to the playlist a rule that says if the song has been played within the last 4 months say, it gets kicked out of the playlist.

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How do I fill a 40GB iPod with random subset of a larger music library?

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