iTunes 18.104.22.168 - iCloud Music Library preference box unchecks itself and other headaches
Long-time iTunes Match subscriber and I have a large personal library (~50k songs) that used to be managed flawlessly. Then numerous songs would stop syncing to my phone. And now with Apple Music, nothing seems to work properly.
These days, I'm not sure what is worse: before the latest iTunes and iOS 9 update, Apple Music tracks added to my iPhone did not show up on iTunes on my Mac at all and most of my iTunes (numerous) playlists would be empty folders on my iPhone. This, despite the iCloud Music Library box being checked in iTunes.
Now, with the latest versions of iTunes and iOS 8, my iPhone and iTunes finally seem to talk to each other (for a few minutes I could see the playlists created on my phone with Apple Music in iTunes), but iTunes seems to uncheck the iCloud Music Library preference box by itself. The craziest instance of this was streaming an Apple Music song that had been added to My Music and it and all the other songs disappeared from iTunes in the middle of the song I was streaming. Bizarre.
And on my phone, many of the pre-Apple Music legacy playlists remain empty, but now there are four copies of the same playlist folder, and in some cases, four more copies with the number "1" appended to the end of the title.
Anyone else seeing this behavior? Am I stuck until El Capitan and iOS 9? Am I just wishful thinking that those upgrades will somehow fix my problems? Given the size of my library and sheer number of legacy playlists, I am loathe to wipe everything and start over.