Robert Scoble, a widely-read weblogger and Microsoft employee, has an interesting view on why you shouldn't buy an iPod. In a nutshell, purchasing music via iTunes (with Apple's AAC DRM) is a dead end because, so he says, Microsoft's WMA DRM is the inevitable winner in the DRM standards war. Needless to say this has generated quite a bit of discussion.
"When you hear DRM think 'lockin'" he says. Very true, but it cuts both ways. Maybe AAC will will in the end, possibly WMA or even a third standard. Or maybe DRM will go away. No one can say for sure, so in the meantime buy the player that suits you best.