I signed back up for an Unlimited account at Rdio for my trip back east two weeks ago. Coincidentally I came home to find the external hard drive that holds my iTunes Library wasn’t mounting. At least I could use Rdio to rock out to some tunes while troubleshooting it.1
Anyway, all of this is to say that Rdio can very nearly be an iTunes replacement. If that’s the route you’re headed, definitely check out Jacob Budin’s Trnsmit. It’s a simple webapp that will move your iTunes playlists over to Rdio.
The process isn’t exactly automated. First you need to export each playlist as an XML file out of iTunes and then upload each one separately to Trnsmit. It’s a start though.
It was just a bum power supply. Drive is back up, and percolating up to Crashplan’s servers as we speak.↩