Random iTunes playlist

I'd like to create a playlist in iTunes that randomly selects a dozen songs from my music library when ever I connect my ipod. (I use my nano mostly for podcasts but would occasionally like to hear some music). Is it possible to set a smart playlist with these parameters?

"I'm trying to do this without the manual deleting of the playlist"
You don't need to delete the playlist just the songs that are in it. Select the playlist and press the Command and the A keys together, this will highlight the entire selection then hit the delete key, that will refresh the list. You can refresh the list anytime you like and it will update the iPod next time you connect or sync.
"I thought I had heard that the ipod shuffle could be set to do this, when docked - have you heard that?
Shuffles don't work the same as the other iPods. For instance there are no "sync music" or "manually manage" settings for the iPod Shuffle. The Shuffle uses slightly simpler versions of these settings where you either choose to "autofill" the Shuffle from a playlist or library or drag and drop playlists or individual songs onto the Shuffle:
Loading songs onto iPod shuffle - Windows
iPod 101: Fill 'er Up

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    iPhone, iPad, iPod touch: Turning off and on (restarting) and resetting
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  • HT1727 how do i transfer itunes playlists on my mac to a thumb drive to use in my car       e in my car?

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  • How Do I Move iTunes Playlists/Settings only to new computer

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    See Recover your iTunes library from your iPod or iOS device.
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  • How do I transfer music from my itunes playlist to my iphone?

    How do I transfer music from my itunes playlist to my iphone?

    Maddening!!!!! What used to work now doesn't!
    Where did simple drag and drop go? Apple invented it!
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  • How can I get my iTunes playlists to sync with my iP4?  Everything else syncs fine but my iPod is empty!

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  • Is there any way that I can have songs in an iTunes Playlist without having the songs play in my regular music list.  For instance: can I have a Playlist of Christmas songs without having them play in the routine shuffle of my music library?  Thanks -Rog

    Is there any way that I can have songs in an iTunes Playlist without having the songs play in my regular music list.  For instance: can I have a Playlist of Christmas songs without having them play in the routine shuffle of my music library?  Thanks -Rog

    Select the songs, press CTRL+I to Get Info, on the Options tab set Skip when shuffling to Yes.
    If you want to the hide the songs from your main music view you could consider changing the media kind to audiobooks or podcasts if you don't mind the side effect of them showing up there instead.
    tt2

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