Back when I was super in to keeping a lossless FLAC music stockpile instead of just using Spotify, I remember all the music nerds using things like id3 namer hooked in to musicbrainz to organise music and things like foobar2000 to play it. Which lets you arrange the ui layout exactly how you want.
Might be worth suggesting he upgrade his tooling to more hobbiest level stuff.
He's computer literate. But not quite that computer literate when it comes to that. I also have concerns about how well supported this kind of thing still is. I used to use mp3tag to do similar things. But as more people move towards spotify, and api's go defunct. You just end up with buggy software my father won't understand what the issue is.
He's also pretty engrained in iPhone and iPad stuff. So the end zone is the album art still has to load in iTunes to show up properly on his phone.
Might be worth suggesting he upgrade his tooling to more hobbiest level stuff.