I toohave the same love-hate relationship with iTunes. SinceApple is the only company offering the iPod Classic which allows me to always be able to travel with my huge collection of music well over 12K songs. If iTunes would disapppear and my second iPod Classic would disappear (yeah my first broke down) I would be f?cked and sad for sure. I have disciplined myself to only play and define various playlists (to reduce my time structuring and increase my listening time) and so I have several playlists for the following moments: different friends fav playlists for our suppers, roadtrip playlists, indie, Icelandic artists, Québécois playlists, St-Jean (our national day), soundtracks, Tarantino soundtracks, groovy, blues and jazz, old jazz, punk, metal, classic rock, alternative, my teens rock, French songs, give me energy playlist for cleaning faster mood… My playlists evolve with my incoming music and help me focus on listening to music…. When I wanna live dangerously, I press on shuffle within my entire collection with no filters to constrain my what I call “surprise me” playlist. This is by far my favorite playlist, its ephemeral status makes me enjoy the unknown succession of music even more… Thanks for sharing your close and personal ways of listening to music Isaac Middle….