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Microsoft, like most companies, wasn't willing to "knife the baby" - they couldn't let go of Windows desktop as the center of the universe and paid the price.
Apple has embraced their products being eclipsed by the natural follow on - and ensured they were eclipsed by another Apple product. Witness iPod to iPhone. Microsoft just couldn't get their head wrapped around that and they paid the price for it with Windows, Windows, Windows!That's why Satya Nadella was a much needed change. He got Microsoft back into being a software company and not a Windows company.
Microsoft as a software company is not a company I'd bet against. Back in the day, much of the best Mac software came from Microsoft.
Booting from external drives on a Mac is trivial. Yeah, it's a pain but just clone your pre-upgrade drive to an external SSD and go on. I had to do that so I can use Aperture for a few parts of my workflow that I've yet to find anything better for (geotagging pics is one - although I only have one camera that doesn't have GPS now and may replace it soon).