Nearly two decades later, have we made any progress? iTunes honestly confounds me. And it seems like the Spotify UI is deliberately trying to prevent me from finding the music I want to listen to.
Winamp is still the best.. srsly. Thats what I use... and on my Android phone I use 'Neutron', which is alright.
Check out webamp if you haven't. It's Winamp 2 in your browser, Milkdrop included.