Smart Playlist does not play new songs. Any clue?

I created a Smart Playlist that referes to another Smart Playlist. This other playlist selects randomly songs that were last played before a certain date. (So if a song from that playlist is played, it is automatically replaced by another one). The newly added songs do not seem to be played at all. I need to restart iTunes to do so. Any clue?

In principal, putting a Smart Playlist into another Smart Playlist will work. However, if the rules of the Playlists are conflicting, that may be why you have an issue. First of all, can we be clear on exactly which Playlists are doing what?
Are you saying that songs recently added to your iTunes Library are:
not in the first Playlist,
not in the second Playlist but are in the first one, or
that they are in the second list, but simply don't play.
or that songs, newly added to the second Playlist are there, but don't get played? In this case, how many songs are in the list?
Can you take screenshots of the two playlists, or list them here. In this screenshot for example;
...this Playtlist refers to five other Smart Playlists. The resulting Playlist is usually over 300 songs. So I don't always know if a song in the list ever gets played, simply because there are so many. I do know however, that the list plays a random selection of my songs and gets updated successfully when I sync the iPod with iTunes.
If you list the Playlists here (rather than screenshot them), can you also mention the top left tick-box section; "match any/all of the following rules". It changes according to the fields below it.

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We recently pruchased 4 new songs from iTunes on the iPhone.
All 4 songs were successfully downloaded. We Sync'd the iPhone with iTunes on a Windows PC. All 4 songs are now in the library on the PC.
We then used iTunes on the PC to add the 4 new items to an existing playlist. For what it is worth, we do all our playlist maintenance on the PC and then sync back onto the iPhone and our iPad because we find playlist maintentance on both mobile devices very clunky and time-consuming.
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*** Update ***
We purchased another song on iTunes today. We added it to one of our playlists on the PC and sync'd the iPad. On this occasion the four songs we added to playlists yesterday all sync'd correctly. However the new song we purchased today did not sync into the playlist. I can't imagine why, but is there some kind of delay built into the sync'ing mechanism somewhere?

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Smart Playlist does not play new songs. Any clue?

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