Even though Apple chief executive Steve Jobs' long-stated desire for DRM-free iTunes music has finally been realized, some observers and users are questioning Apple for the way it's handling certain aspects of the change.
We're seeing several sources warning users about upgrading their libraries until Apple introduces more options. (Not to mention finishing upgrading the entire catalog of ten million songs, which Apple says could take until April).
For example, my library contains 536 purchased items; only several are TV shows, or free singles and music videos of the week. However, the home page of the iTunes Store only offers to upgrade 82 of them.
The number will rise eventually, but what really has folks disappointed is the "all-or-nothing" approach to the upgrade. If I want to upgrade, say, my beloved purchased Athlete albums, I can only do so if I upgrade my tracks by Lindsay Lohan (don't ask) and a karaoke version of The Killers' "Mr. Brightside" I for some reason thought was a good idea at the time.  Looking back, I shouldn't have ever paid for them back then, and I'd rather not suffer insult to injury now.
Yikes.
Also: If you bought a track or two from a protected album that has now gone DRM-free, you can't complete the album unless you first upgrade those tracks. And that means...all of them, whether you still want them or not.
None of the promotional songs I got for free (like the Singles of the Week, or that "Back to School" cross-promotion with Facebook from a few summers ago) are appearing in my upgrade offer, although we have read reports from people who are seeing those. iTunes uses your account's purchase history to present this "special offer", so you'll still spot songs you long ago banished to the Trash in disgust.
The motive behind Apple's moves aren't clear, but for customers' sake, many are hoping the company eventually delivers friendlier options by the time the store is completely DRM-free this spring.