I created an administrative user as requested and that user was able to sync music while signed in to my Music account.
I do have music that I ripped on my normal account. Could those files confuse the sync process?
When I tell iTunes to find "Nude & Rude: The Best Of Iggy Pop" in the iTunes store it cannot, even though that album is there with the exact same name, artist, and date. I have a lot of these albums that I ripped into m4a and mp3 format, how can I tell iTunes how to sync them? Should I move them out and then reimport them?
Could recordings of my own music cause issues? Some albums also have pdf files. All of these things should be relatively easy to figure out, report on, or flag in some way so they can be addressed manually if necessary.