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This is an interesting post on the Windows Mobile Team Blog answering the question "Why can't I upgrade to Windows Mobile 5?".
Quote:
We released Windows Mobile 5 a few months ago and devices are starting to hit the market now. A question I've seen asked in a number of places is, "Why can't I upgrade my existing WM 2003 SE devices to WM5?"
The answer is sure to get me a bunch of angry comments from people who abbreviate our name "M$." You can choose to see this as spin from a greedy marketing wonk, or you can see it for what it is--an honest attempt from a developer to explain how this stuff works.