Workaround for iPhone's Smart Playlist bug
There is a bug (do a search for smart playlist in this forum) with smart playlists not displaying the correct songs on the iPhone.
I just tried something that seems to have worked…
I have a playlist in iTunes called “Recently Added” which I want to keep synced with my iPhone.
I created a new smart playlist called “Recently Added (iPhone)”. The playlist has one rule: “Playlist is Recently Added” with live updating checked.
I now sync this second playlist with the iPhone and all the correct songs show up in it.
and still helpful in 2010. What up Apple?
Note: I sync “Playlist” and “Playlist (iPhone)” (otherwise I get a error from iTunes). Works with podcast smart playlists too.