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A lot of bashing has been going on based on Farhad saying that iTunes tracks cannot be played on players other than iPods and iPhones. Complaints revolve around the fact you can burn a cd and rip that to mp3s or you can use software to capture the audio stream to mp3s. Of course all these can be done with Windows Media DRM as well.
These claims of iTunes compatibility with non-Apple players are kindof like saying your word-processing documents are compatible with MS Word if you print them out, scan them back in and the use OCR to convert the image data back to text in Word. Could you do it, of course. Would you do it, probably not.
Really, how many iTunes customers have burned their iTunes collection to CD and ripped back to mp3 at something like double the file sizes? Even with DRM-free mp3s, I would probably try to convert them to a format with a more efficient compression scheme, which using iTunes would be AAC - and I'm back to using iPods and iPhones only. And how many iTunes customers are customers because they bought an iPod rather than the other way around?
If you are not actively trying to defeat the DRM, iTunes makes it painful to use a non-Apple audio player. The Windows Media Audio format is compatible with a wide range of players (the el-cheapo $20 players can't handle DRM or VBR or lossless wma files, but most reasonably priced players and the pocket pcs can handle those options), but not Apple hardware (without burning to CD, DRM stripping, etc.).
In the end it's driven by your hardware. If you have an iPod or iPhone iTunes is the most viable and pain-free option. If you have almost any other device, a service that uses wma is going to be more convenient.
Ideally, manufacturers would include both FairPlay and WMDRM capability and stores could offer downloads with either DRM scheme. Since MS has licensed WMDRM playback to many manufacturers, software developers, and music services I assume that Apple does not want to licence FairPlay to other manufacturers or obtain a license for WMDRM capability for the iPod/iPhone/iTunes architecture. This would be consistent with their approach to the PC market - hardware and OS only by Apple, no licensing to others.