iTunes feels like more of a dinosaur than AOL did by the early 2000s. AOL at least tried to keep up with the times for a while.
Apple's problem with services is rooted in the way they approach products in general. It takes Apple an enormous amount of time and resources to come out with a product. When they finally come out with it, it's well-polished. But it never really changes after that. Apple lets the product waste away, and eventually it's supplanted by something else. With iTunes you can see that Apple has tried to make updates, but those updates have turned iTunes into a mess, and the core iTunes Store experience hasn't changed. I would say it's gotten worse. Searching is incredibly unwieldy across apps, books, and music, and can't compete with the convenience of streaming unlimited content. Apple has never gotten Internet services. They've shuttered all the online services they've ever created except for iTunes. They didn't improve .Mac; they shut it down. They didn't improve MobileMe; they shut it down. They had to send out OS update discs just to get people to migrate their e-mail to iCloud. Who else has an e-mail service that is reliant on a particular OS?
It seems like iTunes is a chore to them and has been barely kept alive in order to remain compatible with all the devices they sell. If Windows is Microsoft's legacy product it has to maintain for past compatibility, Apple's equivalent is iTunes. But the original iTunes and original iTunes Store were both amazing. It just seems that Apple can't do things well until they scrap something and start over.
Agreed. What I find funny is that Mac.com & MobileMe could still be used as the names for iCloud and it would still make more sense than continuing to call iTunes by it's name. It seems Apple has no problem dropping and replacing product names, but for some reason they have held onto the iTunes name long after it gained more than just Music. On pretty much every tech or social site that isn't Apple based, iTunes is usually seen as a bloatware with an unfriendly user interface and more often than not is used as a punchline. If there is any product of Apple's that would need re-branding it would be iTunes and it's store. I guess as long as profits keep going up due to the natural migration of the public, they don't see a need to fix anything.
QuickTime Player is another application that exemplifies your point. In August, QuickTime X will be 5 years old. It's still pretty much as simple and useless as the day it was first released. I still find myself using QuickTime 7 Player 95% of the time because of the features that X continues to lack.