When is Apple going to completely repeal and replace iTunes with something new?
Question is what that "something" is. I think "repeal" is more likely than "replace" and that Apple will move to syncing everything through the cloud - basically you'll sync photos via icloud, all media will be direct download from iTunes store (available on all linked devices, with local storage as needed), mail/calendar/contacts/etc sync through icloud or other cloud providers. Which leaves owned music (i.e., ripped from CDs), which I suspect they'll drop support for sooner or later.