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Interesting point. Apart from error messages what other features in Apple products are un-Apple like?
Bloated application : itunes. Clunky user experience : finder. Bug ridden OS updates : you know the ones. And best of all, offering two ways to run Windows on your Apple branded hardware : bootcamp and parallels :p

Fortunately, there are also upsides. The ios app store (even if all the major mobile app stores launched in 2008) was a godsend and lifted from linux package managers. At least, that's how I see it.

Black and white is boring. Shades of grey are more interesting. Unless there are 50 of them.

How was the iOS app store lifted from Linux package managers? The main characteristic of Linux package managers, as I see it, is dependency management. Third-party iOS apps aren't allowed to have any external dependencies outside of the OS, so there is no dependency management. Installing an iOS app is just a matter of downloading it and unpacking it.
From dpkg to Ubuntu Software Center, update managers have provided a list of installable software that can be downloaded from a repository, similar in functionality to the App Store UI. (Ubuntu's UI is most like Apple's, but I don't know which came first.)
Weird to call the flagships products un-Apple-like. Do they not define Apple-like de facto?
Apple's Windows apps have traditionally been less polished than their Mac counterparts. I don't suppose there's a team at Apple deliberately sabotaging the Windows versions, but Apple has every reason in the world to focus on the Mac versions at the expense of the Windows versions.
Error messages in iTunes Mac are just as bad.
I'm not convinced that allowing their Windows software to slip in quality - software they force you to use if you buy an iPhone - will improve their brand image or prompt consumers to go purchase an iMac instead.
Side note: I don't think error messages should ever start with "Whoops!" It sounds condescending and unprofessional, at least to me.