If Apple’s going to embrace the cloud wherever possible, it needs to change iTunes too. The program should be simpler. It might be better off being split into separate apps, one devoted to device syncing, one devoted to media playback. (And perhaps the iTunes Store could be broken out separately too? When Apple introduced the Mac App Store, it didn’t roll it into iTunes, but gave it its own app.)
The iTunes we’ve all come to know has had a good run, but it’s reached the point where it is a crazy agglomeration of features and functionality.
I couldn’t agree more, and I’d add one more issue to the list. Right now the iTunes Store is basically just a web site running inside iTunes. It’s slow and a pain to use. Apple should either turn it into a native app, or if they’re going to stick with the web app, at least let us access it inside our web browsers.