How to manage an iTunes library larger than the capacity of my iPod?

I have a 40G iPOD and now my iTunes library is larger than that. When I last synched, iTunes automatically created an iPod list. I'm unclear on how the subset of songs was selected. When I add new music, do I have to manually move things in and out of this playlist, or is there some more clever trick?

If the library is larger than the iPod, it simply selects at random, enough songs to fit.
Here's a better way to do it yourself.
Create a new Smart Playlist.
Match rule My rating does not equal one star.
Limit to 37.5 GB (or whatever) of songs at random.
Songs you don't like rate them one star and they will not get put on the iPod or will get removed next time you sync.
Open iTunes prefs and set to Auto update only selected playlists and select this new playlist.
Also, any songs you do not want to go onto the iPod at all, uncheck them. I do this for podcasts, Christmas songs and such.
When you want to change the songs, simply select this playlist in iTunes, select all the songs and press delete.
It will empty and then fill up again based on the criteria above.
Then connect the iPod and resync it.
This is how I do it as I have ~12 GB of songs and 4 GB iPods.

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