Whether you use i Tunes or update wirelessly, you'll have the same amount of free space on your device after you update.
I found one fix that allowed the sort order to be correct, but disabled the Live updating function of the Smart Playlists.
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.
With the change in i Tunes 8, getting a new batch of tracks to rate is a relatively lengthy process. thread ID=1742897 Kevin Yank Just when I thought I knew everything about i Tunes, I caught this cool hint on Mac OSXhints- The i Tunes search allows search by star ratings.
Simply add *'s to your search with or without other keywords. This makes it possible to find songs by the Beatles with three stars without having to resort to a Smart Playlist. To get the most out of smart playlists, you really need to have complete tag information.
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.