If you’re thinking of downgrading to the new iTunes, stop! The new iTunes breaks the ability to convert the music you’ve bought — even “DRM-free” songs sold at a 30 percent premium — into MP3s that will play on your iPod.
While cumbersome, the “buy-burn-rip-to-MP3” workaround has been the primary way to start with a 99 cent iTunes download and end up with an unrestricted MP3 that will play on your Squeezebox, your non-iPod portables, or your MP3-enabled DVD player (it’s not about “piracy” — if that was your bag, you’d have started by downloading the song as an MP3 from the myriad P2P options).
So iTunes users who have an existing library of songs purchased from the iTunes Store may want to consider doing their conversions before they “upgrade” to iTunes 7.2. (Sure, you can “upgrade” some of your DRMd songs to the “DRM-free” higher-quality AAC format for 30 cents each, but remember that this is not currently an option for the vast majority of iTunes tracks.)
Update: Playlist magazine has more on this: “After testing this further, it appears that this problem crops up only when you rip the CD with iTunes. I took the CD made up of protected tracks and ripped it with Amadeus Pro to MP3 format. I brought the resulting tracks into iTunes 7.2 and they transferred to the iPod without a problem.”
Update 2: Some people have figured out how to get iTunes to load burned and ripped tracks by rebuilding their libraries. (Thanks, Mark!)