Are either of you familar with kodi or remote access /streaming via ssh ? If so one simple option would be to setup a ssh tunnel thru to a music store on your network and have him connect to it via key (preferred) or passphrase ( less preferred for security but doable). that way you would be able to update and / or curate playlists and or even allow him to remotely access a pandora /spotify account form your network / IP and not be technically voilating ToS.