This is the crux of Microsoft's marketing problems. It's not that they aren't good at technical marketing issues, it's that the brand itself is so voluminous, it's very hard for people to connect to specific products like Windows. And the efforts to persuade consumers isolate the tech media and confuse IT shops.
One of the biggest issues network inventory program faced was consumer confusion as to why they should buy an upgrade at all. Microsoft did a very poor job of communicating why anyone should care and added such a complicated set of offerings that people simply couldn't figure out what to buy. (Note that Windows 7 also has a very complicated pricing scheme.)
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