The comparison to Apple kind of misses the point. Apple morphed from being a computer company to a toy company about the time it dumped Moto/PPC/etc. for X86. Computers, per se, are about 10% of the company, and falling. Whatever Jobs did, he didn't make it better at what it was doing, but jettisoned what it was doing for something else.

M$, on the other hand, faced Apple's problem, only earlier. There's a reason why folks opted not to update from XP and Office 2000 (or whichever one they got in the first place): XP works fine for most folks, and most folks use only a fraction (if any at all) of the bells and whistles that have been added to basic WP in Office. Not to mention that Excel was at the nexus of most of the quant crap that caused The Great Recession, London Whale, and doubtless countless other screw ups we don't yet know about.

The, yet again, EoL of XP will be interesting to watch. Forcing a full re-install of all user programs is reason enough to not bother. About 40% of Windows is still XP, and works fine for those folks.

Could anyone, including Uncle Bill, have divined another wintel monopoly that made him rich in the first place? That would require another clueless IBM, another nearly bankrupt Intel, a clueless Lotus, and on and on.