Those of you who remember iTunes when it was new, when it was merely a revamped version of SoundJam MP, will sympathize the most here. iTunes used to be a great tool for playing music and ripping CD's. Then the iTunes music store came along and it was good. Then apps came along and iTunes went bananas. Jason Snell, Macworld's editorial director, argues iTunes needs an overhaul, and I couldn't agree more. In fact, I had a post on this subject (likening iTunes to Vista, in fact) waiting in the wings for two years now, but I think Snell has hit upon the salient points in his article.
Namely: Sync is terrible (and slowly being outdated by pure cloud goodness) and iTunes has become a bloated monster of an application. On a Mac, anyway -- it was always a pretty lousy experience on Windows.
Anyone who has tried to manage more than 50 or so apps will tell you what a pain that experience is, let alone the myriad other eccentricities and failures of interface iTunes provides. One of my personal bugaboos are modal dialog boxes. These are pop up windows that usually feature a choice like OK and Cancel and report something went wrong, but the main thing is they require you to click on them before you can do something else.
iTunes is chock full of these! From errors galore (I don't know that any Apple software I've used in the 30 years I've been using Apple products has ever thrown as many error messages as iTunes) to just stupid things like warning that some apps couldn't be installed (ad nauseam), iTunes is Apple's most modal window-crazy software maybe EVER. It's a huge impediment to progress, in my opinion, and makes for a horrible user experience.
I'd dare say iTunes is the one app consumers simply "put up with" because the rest of the Apple experience is quite good. Also, if you never have errors in iTunes or manage a tiny library, you may never experience too much pain with it. What do you think? Do you wake up each day happy to click in iTunes, or do you dread it like a tooth pulling?