When syncing smart playlists, pay attention to which column you have the ordered the music by.
Which meant that every time an attribute of the playlist was updated (Such as rating a new song for my ‘5 Stars’ playlist) nothing was updated upon syncing with my i Phone. Macbook Pro 1.83 Ghz Snow Leopard 10.6.1 i Tunes 9.0.1 i Phone OS 3.1 If you have an improvement please leave a comment.
This totally defeats the purpose of a playlist that automagically updates my i Phone with the last 100 added, or top rated songs. Alas, after following a suggestion from this discussion thread (Thanks Dave Jelfs! In fact there’s even a bonus side effect for those who only want to sync music, and not video within your playlists. Ctrl Click on the playlist and select “Edit Smart Playlist” A new window will appear with all the settings for that particular playlist. While is is a workaround it does allow for the playlist to be synced, auto updated and appear sorted as you wish on the i Phone.
Resetting a play count in i Tunes is a task that will only take a few clicks of the mouse.
Right-click on the "Play Count" column of the song in your i Tunes library and select "Reset Play Count." You can also reset the play count of your entire i Tunes library by selecting all of the files instead of just one.