iTunes needs a facelift...bad. Not because it's "been a while and something fresh would neat." No. It's because the user experience of iTunes is broken.
iTunes is suffering from some growing pains. When it was first designed and released, it was for organizing and playing music. Now it does everything except mop your kitchen floor. The fundamental problem with this is that unless you "grew up" with iTunes, the interface is now very daunting. It's hard to find things and when you do find what you're looking for, it's been forced to work within the confines of the iTunes interface - when certain things could benefit greatly from an entirely new interface.
Let me demonstrate. One of my gripes is with the iPhone management. Those of you with iPhones will (hopefully) relate with me that clicking endless checkboxes and choosing from dropdowns is a pain. Not to mention how much of a pain it is to organize all these new fancy apps on the iPhone's home screens. So we decided to see what would happen if Apple spent some time rethinking the iTunes/iPhone management layout. We think it should go something like this (click thumbnails to enlarge):