"Microsoft and Windows rightly learned the lesson that touch requires a new UI and paradigm," observed Thompson. "Theoretically, it might be possible to put the two together, but when you are constantly dealing with both, by definition you are using a very sub-optimal interface for each."
A technical solution that fell short
He blamed technologists, the very people who design and develop operating systems. "The tendency is always to want to have the elegant solution, but that doesn't get how real people think and operate," he asserted. "Where technology companies fall down is to think about things only from a technical perspective."
Thompson portrayed operating system complexity as a spectrum. "Chromebooks and iOS are on the left, Windows 7 and OS X are to the right," he said. "But Windows 8 is way to the right of Windows 7 and OS X. It's much more complex."
Windows RT, the stripped-down sibling to Windows 8 that Microsoft intended for tablets, is, to Thompson's thinking, alongside iOS and Chrome OS on the complexity line.
But Windows RT, which powered the original Surface RT and now runs the new Surface 2, and little else, has been remarkably unsuccessful. Most long-time Microsoft partners have either ignored or abandoned Windows RT, instead choosing to arm their tablets with the two-headed Windows 8.1. The biggest blow came last summer when Microsoft was forced to take a $900 million write-off to move excess Surface RT inventory, causing its stock to plummet and make some wonder if it had been the final nail in CEO Steve Ballmer's coffin.
What can Microsoft do now?
The analysts were unsure how Microsoft could address Windows' complexity, perhaps because Microsoft doesn't seem like it has a plan, what with its backpedalling from decisions about the desktop.
"It's difficult to see where Microsoft goes from here," Thompson wrote last week. "Yet there's little question in my mind that the touch environment is hastening the decline of PCs suited for the Windows desktop, even as the desktop ruins what is honestly a rather delightful tablet experience."
Or as Silver put it, "Selling Windows is getting harder and harder."
That's the headwind blowing in Microsoft's face. With stagnated PC sales and little traction so far in tablets, sales growth of Windows licenses to device makers, which provide the bulk of the company's revenue from its flagship OS, will likewise stall.
When asked how Microsoft would address its Windows problem, Directions' Miller replied with a Delphic, "That's up to Microsoft, isn't it?" But he pointed out that the Redmond, Wash. company has a big card up its sleeve.
"Office made up of very light-weight [touch-enabled] apps, that's their first big chance to show what you can do in the Modern UI," Miller said, referring to his argument that there has not yet been a Metro app of sufficient necessity to give customers a reason for using the UI.
Sign up for CIO Asia eNewsletters.