More for my own reference really, but this might be useful to others – certainly been driving me mad enough over the last few weeks!
I’ve got an iTouch 64Gb and have previously been synching it with iTunes 8.x without issue, but on upgrade to 9, all of my “most played”, “most recently added” etc playlists suddenly show random tracks (on the handset only).
This is down to the issues described at: http://discussions.info.apple.com/thread.jspa?threadID=2227108&tstart=1.
Basically, to cut a long story short, you need to add this option to each playlist with a “limit” set:
Re-sync and voila, life is sane again. That said the performance and literary of niggly bugs with iTunes (as well as the heavy handed updater) is getting on my nerves. Roll on Windows Mobile 7!