I’ve finally settled on a new way of listening to music at work, which is where I do the majority of my listening. Instead of listening through iTunes with my iPod, I now listen to Pandora primarily and once I find a new band I like, I open Spotify, add all their past albums and continue listening to them through there. I tried using Spotify as my primary listening software but I like the shuffle/radio-ness of Pandora.
The big downside to Spotify is that it currently requires a Facebook account to login. I had cancelled my Facebook account about six months ago but I created a throw-away account just to get Spotify. It’s that good.