What makes iTunes’ deficiencies so infuriating is that the program is indispensable: it’s the nerve center that stores all of your Apple-related media content, mediates all of your Apple-related purchases, and connects all of your Apple devices.
There’s no way it’ll be Apple’s undoing, but iTunes is certainly Apple’s single worst piece of software (ok, maybe second worst after iMovie). And it’s made all the worse by the fact that Apple depends on it for everything.
There are two ways out of this. One is described in the article, and that is to stick in 2 pieces of dynamite, blow the thing into the next life, throw a party, and start fresh. That’s not going to happen, Apple has too much invested in iTunes. The other more likely scenario is to move iTunes from the desktop and into a cloud service, letting the desktop app die a slow death. Google seems to be following this strategy and I can see Apple doing the same, especially with that new data center they’re building.
Whatever happens, I don’t think iTunes can continue being this gigantic catchall for all of Apple’s devices. Eventually the full weight of everything it’s carrying will cause it to collapse.