Too Much Music for iPod Nano

Hello everyone,
I need help adding music to my Nano.
I used to have a first generation Shuffle, which automatically chose music from the iTunes library when I plugged it in. It tended to choose music randomly so that I had different songs from many albums.
I now have a Nano and would like iTunes to randomly pick music to add to my Nano (since my music library is too large to fit on the Nano). However, when I plug the Nano in, it creates a playlist, but chooses entire albums.
Is there a way to make this more random? I thought it'd be neat to sync the Nano with the Party Shuffle Playlist, but iTunes won't let me.
If anyone can help, I'd really appreciate it.
Thanks!
Allison

How about a workaround which requires two steps to update:
Create a single playlist, set it to Play Count is less than 900000, limit to the number of GB or number of songs that will fit, selected by "Random". Sync your iPod to this list.
When you want a new random list, edit the Smart Playlist and change random to "Album", choose "OK", then edit it again and set it back to random for a new list of songs to sync.
Hope that helps
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