Stross (who also wrote a fine item in 2005 about why Sony didn't build the iPod) has some basic points: DRM bad; iTunes Store has DRM; look at Plays for Sure and all the Microsoft customers that got rogered; iPhone bad; eMusic and other unencumbered music sales online, good.
While I have no real love for FairPlay, and I do worry that my iTunes purchases might not survive future device changes, I couldn't quite put my finger on the core bogosity of his thesis. As is often the case in the Mac-blogosphere, John Gruber got his opinion out of his brain with more speed and pith than I could muster:
You can "pledge a lifetime commitment to the iPod" and never once come into contact with a FairPlay-protected song or video. If you don't like FairPlay's restrictions - and there are plenty of good reasons not to - then don't buy any, and rip your music from regular CDs.
iTunes Store music and video locks you in. iPods and iPhones do not.
More after the break...