Hi. I don't think things are going to get any better. I'm running running iOS 12.x on an iPhone SE and iOS 13.x on an iPhone 7+ with the Catalina beta and on a recent synch completely destroyed my playlists on both the iPhone SE and 7+. My purchased iTunes music was okay, but all of the older DRM and some of my older iTunes music purchases will not synch. On top of that, my music that I transferred from my CD collections will no longer play.
On a reset of the music app on the iPhone 7+ completely stripped out my playlists on the Catalina music app, and I had to reload the playlists from a saved playlist file. When I tried another synch on both iPhones, I'm getting the same error messages, won't synch the DRM, some older iTunes purchases and my entire CD collection will not synch.
I tried an experiment with an older iPhone 5C to see what happens to the playlists on Catalina, and, same story, the playslists are corrupted and the 3 types of music will not synch or play.
I looked at some of the corrective actions on some of the other forums and at some of Apple's own solutions and it seems the only way I'm going to be able to play at least some of the music is to upload the library into iCloud. This will not work for me as just my music library (including my purchased music videos) is in excess of 350 GB. An upgrade to iCloud music is 200 GB at $35.88 a year and then storage goes to 2TB at $119.88 a year.
Before the updates and beta experimentation, I could synch my music to any of my supported devices and listen to everything for free. After the updates and betas, I feel like my music is being held hostage and I have to pay a ransom ($600 over 5 year, $1200.00 over 10 years) just to be able to download and play music on my devices for content I've already payed for.
My current workaround is loading my music on to an old android phone I'm using as a media player (love that 128 GB SD card) but this won't play any of the old Apple DRM and unless I invest in a 1 TB SSD (which I won't) I can't get my whole library in there. Also, my playslist won't transfer over for some reason, and I don't have time to build playlist just for an old 'droid phone.
With with all these recent changes, I've lost 3/4 of my iPhone Apps, lost 1/3 of my music (on my devices) and a gained a lot of frustration. Too bad Time Machine can't really be used as a time machine, I would really like to go back in time when things actually worked.