[TheRealNGenius]

True, these things seems intentionally made complicated since they want to push Apple Music/TV subscriptions. If you still haven't figured it out, you can put iTunes music to your iPad. But it requires like ~$20/year subscription called iTunes Match. So yeah, you can't do it for free using their suggested methods.

[_ph_]

Well that is the point, I have the Apple Music subscription which includes iTunes Match. So that is, how my music all got into Apple Music in the first place. But later on, it deleted some tracks I cannot add back. At least for years now, I am looking for a way how to do it. The problems only started, after I subscribed to Apple Music.