>Apple went from being a leader in the music-listening industry with excellent UX to trying to compete with Spotify and YouTube, who are frankly not even that great

They might "not even be that great", but they are where all the listeners and the money are.

Ripping, listening to non-streaming music, etc, is becoming rapidly a hobbyist thing for older generations and a minority of hipsters. The whole rise in music industry profits in the last years was in the streaming area, purchases and digital downloads are down.

So anybody touting some specialized device, that takes ripped or bought mp3s, etc, is mostly living in the past as far as the market is concerned.