Wont play unchecked selections?

Question

I'm having a problem.
I have a 1st generation iPod nano which is 1 gig, and hardly anything fits in it so i decided to make sure it only synced checked selections. When i put iTunes on shuffle, it played the unchecked songs, but ever since i updated it, it will only play checked selections.
Is there anyway i can make iTunes play both unchecked and checked selections while my iPod only syncs checked selections?
Any help would be much appreciated.

Answer 1

To answer your question, no you can not have unchecked songs play automatically in iTunes.
Instead what you want to do is recheck all those songs, then create playlists of just under a Gig and set up your iPod to only sync that playlist, not your whole library. Now only a some stuff goes on the iPod but also everything remains checked in your library.
An idea for a playlist might be something like this...
Shot at 2007-07-30
In this playlist it auto fills up to 900MB (since a "1G" nano is less than a gig. You can modify that number to whatever works for you) and it fills it up with the stuff that has been the longest since you last played them (this will also include any new/unplayed tracks). As you play songs, when you update the iPod, the playlist will automatically be adjusted to remove recently played songs and replacing them with songs that have not been played in the longest time (or at all), so you get an automatically changing/updating selection of songs on the Nano AND can leave everything checked in your library.
Patrick