It does a great job of getting you from zero to an app, but it breaks down terribly once you try to do anything custom with it. The fact that it hides code from the developer drives me nuts.

I won't start a religious war here, but IB is awesome in demos and less awesome in real world. Versioning alone is enough to make you go crazy (especially back in the .nib days!).

It's worse on Windows. The Windows version would hash file names or something. Probably to get the search features working. So once you imported your files you didn't know what was what. The Mac version probably just uses spotlight and file names were always readable.

> iTunes was awesome on Windows when it came out

It forced a bundled QuickTime install (still does I believe), and back then, it tried hard to become the default media player on your system (even reverting your "no" choice after updates). This led many people to remove QuickTime, only to discover now their iTunes refused to work. It would fail halfway through sync's and upgrades of iDevices routinely, had a generally pretty buggy interface that wasn't very responsive most of the time. It's iDevice backup process was cumbersome for normal users, and often failed without the user knowing (leading to very upset individuals when they needed to restore but couldn't).

Now it seems every new version redesigns the UI in major ways, causing even long term users to not know what to click, etc...

If you really just listen to music, maybe it's fine. For all other purposes, it was/is horrible, however I can't complain because it generated quite a lot of work for my side repair/contract business back then.

I had whatever version was around when the video ipods came around (and a bodgy bit of hardware that was). I couldn't sort videos the way I wanted to - itunes says that that file extension means "tv episode" instead of "movie"? Sorry, it's a tv episode. Not to mention the terrible UI with tiny targets that doesn't blend in with the user's desktop theming. Maybe that was v4+, but all I remember is hating to use itunes (including managing updates as already mentioned)

The software that went with Microsoft's Zune media player was amazingly good. Sadly, even though it was available separate from the Zune hardware, almost nobody downloaded and tried it.

Steve Jobs publicly mentioning only praise about things Steve Jobs made? Unbelievable!

I can only conclude that the people sending such letters had only previously used GTK+ apps on Windows or something.