It's a hella pain in the butt to download and manage music files and I stopped doing it a while back.
All my music is on Youtube playlists, which you can access on any device from anywhere with a Wifi. All you need to do is get into your Youtube account and into your Playlists. If you use Spotify, I can't help you. But for me, there is plenty of music on Youtube, so I don't need Spotify. You don't need an Ipod. You can play the music from Youtube playlist on your phone. Much less hassle.
Can't listen to music while going for walks, but I don't care. It's too much hassle to download and transfer to different devices.
Sorry if this is not helpful.