The 2005 version of iTunes that ran on my PowerPC macbook was strictly better than the app that I have installed today on my Windows 10 gaming PC. The 2008 iPhone iTunes app was better than the "Music" app on my iPhone today -- when I open my phone in airplane mode on a flight to listen to music, it bricks itself for 10 seconds trying to get wifi connection and prompt me to pay them for their crappy music streaming service. There is no way to disable that self-bricking advertisement.
I suspect that the average Apple employee uses Spotify to listen to music and doesn't have a large personal collection of songs not available for streaming on common platforms. The lack of dogfooding shows through.