I gave up on Windows about 10 years ago. I've had to use it for work sometimes, but the Windows Updates are actually destructive sometimes, and often take hours to install during business hours (especially if you happen to need to reboot before an important meeting...). I can't handle uncertainty in Software, and I think that many business are losing productivity because of this. Or maybe IT support departments are happy to keep themselves employed.
Sadly the Linux ecosystem (baring the kernel and the GNU supplied coreutils) do not seem to do any better. And from what gather, Apple is notorious for breaking things as they see fit as well. Not sure how well the BSDs do in this regard.
I am a Debian sid user, so I know well what you mean, but as long as you don't do a kernel upgrade, Linux has been extremely stable for me. This wasn't always the case. 10 years ago, Debian sid would break all the time, but I have probably had only one or two non-kernel/driver related issues in the past 5 years.
Another subtle difference is that on Linux platforms, you have more control over when/how to update, as well as visibility into exactly what is updating. I'm sure it's visible on other platforms, but I don't have to worry about rebooting my machine and having to wait 2 hours for it to come up.
Perhaps another point worth mentioning, LTS versions of Linux distros (Debian stable, or Ubuntu LTS versions) mainly get security patches, and, optionally, back ported software. That makes your OS stack super stable!
I'd put kernel upgrades into a different bucket... but most users don't need to update their kernel on a daily or even yearly basis except for security patches.
Great point about coreutils too! No need to update ls and grep...
