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But there are many rewards to wrapping these products up. MS did well with their little tabbed UIs and checkboxes. It felt more like a mixing desk, easier than say discovering and typing command line options.

I don't think people have a 'this should be hard to use mentality'. I've been with programmers and designers who have had not one idea about designing the interface. They are fine cloning, but not at innovating. And frequently the UI is just born out of cluelessness. Or with websites, the design constraints sometimes override the ergonomics, or even kill code orthognalness.