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I actually think it's a pretty okay marketing strategy. If you truly believe your own interface is a selling point,then you need to show it off to people who aren't familiar with it.

If iTunes truly has a superior user experience (ha!) people will think, hey wouldn't it be nice if all my apps were like that.

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But superior user experience comes in no small part from familiarity within the ecosystem. Material design on iOS is alien mainly because most iOS application behave in the same way.

This is the same for Office on OSX. Since most of the OSX apps have the same look & feel, having an application that is even slightly different is jarring.

On Windows though, it seems to me that most of the applications have gone the way of re-implementing their UI. This does not make iTunes on Windows any less horrible though, but it seems like a case of broken windows theory.

"If iTunes truly has a superior user experience "

It has not

I thought the parenthesis made that quite clear.

Anyway, in the early days of iTunes on Windows, the design and looks was a big selling point.

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