Variable length playlist to fill remaining space on iPod?

My Nano always has some room left after I've synced my selected playlists. Is there a way to get iTunes to fill the remaining space on the Nano - perhaps using a variable length smart playlist?
(I know I could create one giant playlist that draws from my individual playlists and set the size equal to the Nano, but that won't work for me - I need individual playlists for the Nano to work in my car).
Thanks.

Also, it seems that iTunes is not smart enough to -remove- songs when you add something new, i.e. movies or podcasts, and will constantly tell you that the iPod is full. That results in having to un-check the option, remove every song 'automatically added', add the new content, then re-check the "fill free space" box. Did no one actually test this feature or is it done on purpose to wear out your iPod quicker?

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