iPod not syncing from iTunes library I have ~350 GB of music. I recently bought a iPod Classic (160 GB).

When I try to sync the iPod with my computer, it produces a "Not enough space" error, and copies no music to the iPod.

I would expect it to sync some portion of my library, and ideally rotate the synced portion every time it is connected.

Is this normal behaviour, or is something broken?

If it is normal behaviour, is there any way to make itunes sync a random subset of the music in my library, until it fills the iPod?
I believe that you can create a smart playlist, limit it to 160 GB (chosen randomly), and then choose to sync only that playlist. At least you can do something like this with an iPhone.