Like I really want to deal with torrenting, Plex servers, etc. Been there done that. I travel a lot and don’t want to deal with downloading media ahead of time.
I also stopped pirating music the day iTunes was introduced
You do know that iTunes just sells MP4s, right? They work in VLC. You can replicate your iTunes library to a NAS trivially and have it Just Work (now, the iTunes client isn't very smart about network drives, so you're better off having a local library that's backed up to said NAS, but that's not the issue at hand).
What if your CC on file expires?
Well I guess you can just ask (beg) if you need assistance accessing 'your' music library