Hey there, sorry for this trouble. Just writing in to say I don't think you're alone with this problem. I've been looking into a similar, or the same, issue for a few days now. In my case this is on an iPhone 11 Pro Max and an 11" iPad Pro, both on iOS/iPadOS 13.5.1. It doesn't seem to affect my MacBook Pro however, but that is actually still on Mojave 10.14.6. I subscribe to Apple Music with a Family plan and have for at least the last year or so.
The problem seems to be an inability to consistently download songs that have "Matched" or "Uploaded"
iCloud status. While you can't view the iCloud status of a song within the Music app on iOS (to my knowledge), you can on macOS. In iTunes or Music app on macOS, select the song and then press command-I to view the information panel about the song. You should see the iCloud status of the song on the
File tab. For example this song was Matched:
And this one was uploaded:
No songs I have with either of these iCloud status values download consistently for me. I see the same nonsense as you when I initiate a download on either my iPhone or iPad: just a bunch of spinning. Sometimes I get partial circles. Sometimes songs actually download and if they do it takes for-ev-er. However, songs that are directly from Apple Music, e.g. have iCloud status = Apple Music, typically download fine.
To try to remediate this I've tried all the things you have done as well, including:
- Turning Music Library sync off and back on
- Resetting network settings on device
- Restarting home network
- Trying other networks (cellular and WiFi)
- Restarting the iPhone and iPad devices, more times in the last few days than the entire year-to-date prior to that
The only other person on my Family plan is my wife and she doesn't have this issue but she also doesn't have Matched or Uploaded content in her library. All of her stuff is exclusively from Apple Music's catalog.
Essentially my older music library, which is what most of my Matched and Uploaded content is, is being held hostage lol. I think I will be having to get on the phone with Apple.
It's important to note that this seems to affect only downloading of the music. Streaming it is not an issue.
Lastly, I've attached a video showing the issue here.