How to synchronize large playlists with ipod?

can i set itunes to synchronize with all playlists even in the case the ipod disk can‘t match the size. i want itunes to pick titles from all playlists by random each time the ipod connects with itune to be more excited on the go without the hassle of editing playlists for synchronization.. possible?
MacBook Mac OS X (10.4.8)

Change the one where you limit it to 200MB to read...
Limit to 200 MB selected by Least Recently Played
which only uses songs that either have not been played yet at all (new stuff added to the library) and stuff that has been the longest since you last played it. Now as you listen to music on your iPod, those songs go from least recently played to being the most recently played. When you sync back to iTunes, those songs (assuming you have live updating checked for the playlist) will be removed from the playlist and replaced with different ones. So a constantly changing playlist.
I have a playlist set up this way which I called "Been A While" and my rule is...
Limit to 200 songs selected by Least Recently Played
Your 200MB may limit you to only 40 or so songs, if that matters to you.
Patrick

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