If I may inject into this thread, as I've been wanting to get iTunes Match ever since it came out: However, given Apple's QA standards right now I thought it might be best to ask what other's experiences have been like. No customized metadata (other than sorting and SoundCheck, which I'll probably clear before syncing) that I'm worried about losing. I don't think I have anything weird going on in my library that would trip it up. Since I'm also a bit low on space on my phone and I'm not due for an upgrade until next year, I'm wondering if now is a good idea to move to iTunes Match. I'm sure iVolume still does a better job than iTunes does at normalizing volumes, but my understanding is that iTunes Music isn't as dire as it used to be and I don't have much hope that iVolume will see an update. I don't think the script does anything useful anymore since I believe albums by an artist are sorted by release date in modern versions of iOS anyway (are they?). I thought this might be an opportunity to examine my habits to see if they still make sense and possibly move to iTunes Match. Both are currently broken since they depend on finding iTunes which doesn't exist anymore.
On any new music I bought or imported, I would run a script to update the sorting tags and run iVolume to set the SoundCheck tags. I synced everything through iTunes no cloud stuff involved.
Due to poor diligence on my part in thinking through everything, my music workflow is a bit broken under Catalina.