This has been bugging me a lot, too.
The play counts update for me as well as ratings regardless of what device I use, however, the most important metadata to me, the "Last Played" dates, do not transfer from ios devices, just local mac dates and times for me. Of course, the "Last Played" dates are the backbone of all my smart playlists that don't function correctly anymore ever since iCloud was introduced. Hope that this can get bettered.
Miss the syncing of my smart playlists so that the music stays fresh rather than replayed over and over.
Any of you find that the music from playlists will replay sporadically, too? Playlists with 100's of songs in them will be playing on iphone, I'll hit skip, and then it starts it all over again as if I hit the skip back button. Or it'll play the next song, then after that, goes back to previously played song. Quirky service.
Wish I had a fix to contribute rather than just a complaint, but really hoping they could iron this out or provide a work around other than not using iCloud. Here's to hoping!