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Minor annoyances perhaps, but imagine if Apple does fall from its position of dominance in 5-10 years. We'll be stuck with all this music that will only play on their stuff. You'd hope they'd be good guys and eventually let you convert their DRM music into the non-DRM variety, but who knows if they would.
I haven't bought a DRM iTunes track in well over a year. I use Amazon's store, even though it's slightly more of a hassle, because it's DRM-free (and better quality, and usually cheaper to boot).
The general public at large does not care about DRM because they most either don't know what it is or don't have time to worry about such things -- they just want their stuff to work. But if by some chance Apple isn't the dominant media playing company of the future, they're going to be pissed off when the music they bought all those years ago on iTunes doesn't work anymore. Sure, they could burn them on CD and then re-rip them or use an illegal method to crack the DRM, but some people have bought thousands of songs on iTunes without realizing the potential bind they'd be in later.
On the smaller level, I really hope this is announced tomorrow because I can actually start using the iTunes Genius sidebar feature as intended. Right now I play a song, see what it recommends, and hop over to Amazon to buy it. Would love to cut out those additional steps.
I've got an iPod, but I've also got a Sony Ericsson phone, and a SqueezeBox. They can all use use AAC but I prefer FLAC for the SqueezeBox.
I could swap the iPod and Sony Ericcson for an iPhone but as the bluetooth support in the iPhone is borked (no A2DP) I wounld't be able to play my tunes in the car - they come straight from my phone via bluetooth to the car stereo.
So DRM is a big deal to some of us - the lack of being able to by high quality music e.g. flac, online is a bigger one.
I imagine, like you said, you havn't had any problems because you're an "apple fanboy".
I have never own an iPod though I own two MP3 players, one Phillips, one Sandsa. I guess t's a good thing I didn't buy my music through iTunes though since I'd have been stuck buying an iPod.
Not to mention I prefer using Windows Media Player to organize my music. Also I'd have been screwed during the year long period where iTunes and Quicktime got jacked up and I couldn't use either (also couldn't uninstall or reinstall). Ok yeah, if I had a library of music to play I might have been more diligent about fixing the problem but I wasn't tied to that player or device so I didn't really care.
Why?
I don't have near the amount of content you've purchsed, but have experienced the inability to play music I pay for when I want. This generally happens after moving machines, or getting new devices. Just the other day, I had to restart my Apple TV to play a purchased movie. It appeared white during playback. I wasn't doing anything strange. That's when DRM really fails - when I want to play my content when I want.
I have a large library of mp3s. Partly because, I took the time to burn my CD collection which I started in 1987, to mp3, along with some old rare vinyl, and partly because I get sent many CDs to review and play on the Internet Radio Station I an co-owner of.
I don't use iTunes, and I don't have an iPod. What I did get a year or so ago, was a Sandisk player. It works fine, supports DRM, and Audible (I am a member). I signed up for Napster. So far so good. However, I then bought a Blackberry Curve. I put an 8GB micro SC card into it, and I can use this as my audio video player. As both my car audio and the Curve has A2DP I can enjoy stereo audio in the car quite easily. However, I can't play any DRM stuff.
To cut a long story short, I cancelled the Napster membership some time back. I have purchased some DRM free) music via Amazon since then. I haven't bothered with iTunes, as I don't have, or need to buy, an Ipod.
Here's the counter argument - as someone who owns a bunch of devices that don't support Apple's DRM, DRM matters a lot. it's one of the reasons why until now I have bought exactly 0 songs from iTunes.
I'd rather order the CD and be able to rip (and re-rip) it into whatever format(s) I choose. Pay once, play many. The pay-to-upgrade path for iTunes doesn't end here, even if DRM goes.
While the amount of music I bought from iTunes over the years isn't huge, it's still a consideration for me. And I find myself loath to have to buy all my music again just so I can stream it effectively. Anyway, those are my thoughts.