This was terrific and thoughtfully written. Thanks for taking the time to write it!
A couple of other reasons struck me as crucial for why MS didn’t win or come close to winning this:
- They didn’t own the hardware stack. The unification of this division happened when Apple demonstrated that it was worth giving up hyper-precise typing with a tippy-tappy keyboard in exchange for the benefits of a big, bright, touch display. Every other device maker in the world followed, which allowed Microsoft to innovate. But until then they were constrained by other device manufacturers not being innovative. I think you’re spot on that consumers were driven by aesthetics/hardware with their cell phone much more than they were with their beige box PC. Windows stood for compatibility in the early days of the consumer PC market, but in a market where nothing except SMS and phone calls was standardised (and even then, not brilliantly), nobody gave a shit about compatibility. Especially since the best you could hope for was your phone being able to run a J2EE app!
- Inspite of the above, MS were out-MS’d by RIM in my opinion. RIM aggressively locked in enterprise customers to what was once the only game in town (BBOS) and when iOS started to get enterprise features (Exchange support wasn’t even in iOS1!) they still owned the business space for a few years. Easy to say with hindsight, but Microsoft could very easily have been ‘the Microsoft of mobile’ if they’d bought RIM and used it as a springboard for Windows Mobile.