ITunes library is larger then my 60 MB iPod

Is there a way, whereby iTunes can automatically "re-cycle" the songs on my iPod so that eventually I can here them all on my iPod?
What heppens right now is that iTunes automatically creates a playlist based on, what it calls, "our prefernces" (which is basically the number of times a song was played in a descending order)and this playlist is fixed and synced to my iPod. It does not seem to be changing, thus leaving a great number of songs out of my iPod.

Create a Smart Playlist, make the rule to be Limit to 50GB selected by least recently played. Check the live updating box (uncheck the top box) and use "only checked items" if you like. Like so...
With the iPod plugged into iTunes, set it up to update only selected playlists, deselect that one iTunes made and pick this one instead.
I picked 50GB because a "60GB" iPod really only holds about 55+GB so 50 is a good number to give you a little spare room. Make the number smaller if you want to have other stuff on the iPod like videos. Or make it larger if you want to cram it full.
Anyway, the idea is as you listen to music on the iPod, when you re-update to your computer, those now recently played songs get removed from the playlist and replaced with other songs that have been longest since they last played. Eventually you will work through all your songs and they start to reappear, but that can take a long time.
Patrick

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