Smart playlist not updating

I've found that a smart playlist that contains other smart playlists won't update on my phone even with live updating checked. I have to resync my phone with iTunes to get it to update.

Say I have two playlists, one with 100 songs selected by "least recently played" and another with 500 songs selected by "least often played." Both of them have live updating checked. If I listen to either playlist alone, it will update. For example, once a song from the "least recently played" playlist is played, it is removed from that playlist and another takes its place.

But if I have a third playlist that has criteria "(Playlist = 'least recently played') OR (Playlist = 'least often played')" it won't update. In other words, if a song from "least recently played" is played, it is removed from the individual playlist, but it won't be removed from the third, combined playlist.

Is there any way I can get that third playlist, the one that contains two smart playlists, to update?