I have set up a new playlist that seems to update in iTunes and on my iPod.
I have set it up to be :-
Last played is not in the last 20 days
+
My rating is greater than 3 stars
+
Play count is less than 2 (will need to be updated in time)
Limited to 25 songs with live update turned on.
It continually updates the list in iTunes adding a new song when it has played one from the list.
On the iPod it does not do this, but when it stops playing the playlist it selects a new list of 25 songs ready to be played.
When I sync the iPod it transfers the records on the one's it has played and they don't appear in the playlist in iTunes.
It is a great way of playing your favorite but underplayed music. When you have over 6000 songs to choose from it helps.
Ian