Also, in many years my amount of downtime due to Debian's unattended-upgrades is exactly 0. The same cannot be said of Windows updates.

I'm still hoping Microsoft see the light on all the telemetry and forced update nonsense before the Windows 7 cut-off in a couple of years. The trouble is, I can't see it happening as long as Nadella is at the top, and I can't see that changing as long as the big enterprise customers who aren't subject to that kind of nonsense are propping up the share price.