macOS Catalina, the new Music app. This update royally *****. It updates slower, it writes multiple entries for the same playlists to my devices, I could go on. But to the point: I store a copy of my music on my phone, an iPhone 8 with 256Gb storage. I played 20 songs on my phone today. When I got home I plugged in to sync, which took 10-15 minutes. I looked at my playlist, because I update the playlist to rotate the songs I listen to, to hear new stuff. No change. Nothing shows today's date at all. What's up?
My iPhone has iOS 13, the latest updates. I installed Catalina on my Mac Mini two days ago.