ICloud – Why is this one playlist unable to be synced with iTunes Match

Since I got the Tumbleweed badge for this, I'll respond with what I did.

1. Cleared all the star ratings from my entire music library.
2. In each of my "genre" playlists, assigned every song a rating of 5-stars
3. Created a smart playlist that includes every song with 5 stars. This playlist will sync over iCloud to my iDevices for listening.
4. Created a second smart playlist that lists every song in my "genre" playlists that doesn't have 5 stars. This playlist is for maintenance and is only available on my Mac.

This works as long as I do the following:

1. Continue adding songs that I like to my "genre" playlists.
2. Every once in a while, check the second smart playlist, and give a 5-star rating to any songs in it. It will then be empty, and the songs will automatically be added to my listening playlist.

Turn off iTunes Match on the iPhone and synch your playlists/songs via iTunes. After synchronisation turn iTunes Match back on. You will receive a warning message, but your synchroniszed songs will stay on the phone (you can easily verify that by checking the cloud icon, which should not be there).

The only important thing is, that the songs you've synchronize must be part of your iTunes Match library. Else they will vansih after re-enabling iTunes Match.

For me that works perfectly fine.