Re: iTunes Match Deletes Playlists
Yes the same thing happened to me. It turns out that if a playlist contains only songs that are not part of the iTunes library, and you have Music Match turned on, then when syncing to your devices that also have iTunes Match turned on, the playlist doesn't sync. When you turn iTunes Match off and back on, on any device, it asks if you want to delete or merge the content of that device. No matter what choice you make from this point forward that device doesn't have the playlist (because it's not part of the iTunes library) and is therefore removed from your other devices as part of the sync. It sucks and I learned the hard way after having 90% of my playlists deleted and random songs deleted.
Rules to live by in the Apple iTunes Match / Apple Music world:
1) Make sure all songs on your primary device (such as your laptop or Mac or whereever you run iTunes) are synced to iCloud first. If some are listed as not able to sync (little cloud made of dotted lines) then you need to reencode the song at a higher bit rate above 128kbs. You can do this by burning it to a CD then importing it again at a higher bit rate. Again this totally is B.S. and an F***ing waste of time, but it works.
2) Create playlists that contain only songs that have been successfully uploaded to iTunes Match and uploaded to the cloud.
3) Now turn on music match on your phone or other devices and wait and wait until they wirelessly sync. This could take hours depending on how much content you have.
4) Don't merge anything otherwise you get duplicates.
5) Never sync using the lightning cable connected to your computer. This would require turning off iTunes Match on your phone and deleting everything you just synced. IF you do turn it off and on again, don't merge or you get duplicates.
6) Cross your fingers and hope Apple makes this whole process a bit more user friendly in their next updates.