Apparently, at some point today (while I was sick in bed waiting and hoping for death to come), Apple announced that it was switching its iTunes store music tracks to DRM-free versions.

Fair enough, but nothing special: Amazon has been selling DRM-free MP3 downloads for a while now. And I switched to Amazon about a year ago, partly because of an exceptionally good example of customer service, but mostly because they sell standard, unlocked MP3 files with no strings attached.

Now, I don’t have any major problem with DRM in principle, as long as it’s done reasonably. As somebody whose livelihood is based on digital downloads at the moment — and who’s seen his work being distributed on torrent sites, even though the pricing structure and availability of legal versions couldn’t be more reasonable — I recognize the importance of making sure people are compensated for their work. One of the reasons I had to stop reading Boing Boing was because of the rabid and sanctimonious anti-DRM sentiment, and the glee they seem to take at the sight of people breaking end-user legal agreements.

Plus, from a purely practical standpoint, I’m just barely inconvenienced by it. I’m a model Apple customer with all the pre-requisite Apple-branded hardware, and they’ve kept the licensing reasonable enough that I hardly ever run into problems. So it’s not onerous, but still: if there’s the option of a locked or an unlocked version at the same price (or lower) and the same level of convenience, I’ll take the unlocked one.

Here’s the problem: before Amazon opened up its service, I downloaded quite a bit from iTunes music store. Apple offers a “special offer” to “upgrade my library” to the DRM free versions, for 30 cents a song, or 30% of the album price. When I last checked, it would cost me over $100 to upgrade my entire library, and the figure keeps going up as they update more of their database. If it sounds like I’ve bought an obscene amount of stuff from iTunes, that’s because: a) that’s over the course of several years; and b) I’ve bought an obscene amount of stuff from iTunes.

But you can only “upgrade” your entire library, not individual tracks or albums. And even worse: that includes everything you’ve ever bought from the iTunes store, regardless of whether it’s still in your library. Over four years, I can get a lot of stupid stuff — albums I’m not sure why I bought in the first place, songs I wanted to hear at 2 in the morning but never want to hear again, stuff that seemed like it’d be good but turned out otherwise, and just plain lapses in judgement for which I have no excuse. Most of those got deleted long ago, and they’re not missed. But I’d get to pay to download them again if I ever wanted to go “iTunes Plus” for the stuff I still like.

Or, buy them again from Amazon and end up paying less overall or more per track. Which is the confusing part: it seems like it’d be in Apple’s best interest to get some more money out of me, instead of insisting on $100 or nothing.

But as I said, the DRM stuff is no more inconvenient to me today than it was yesterday, so there’s no compelling reason to “upgrade” at all. And it’s not as if re-buying music is a totally alien concept: most of the stuff I got off iTunes in the first place was from albums I’d already bought in college and had to sell back for textbooks or food. So in the end, it’s just another example of weird business practices by Apple. And another weird side effect of living during a cross-over from one type of media to another. (Expect to hear me complaining more loudly once all the video content starts going DRM-free).