I routinely use Linux (Arch, Gentoo, Ubuntu, CentOS, several others) Windows (98 - 10 (yes, really 98), server 2000 to 2016) and I speak quite a few other OS dialects (NetWare and FreeBSD fex).
The worst for updates, by far is Windows 10 and server 2016. I'd better qualify that. Gentoo can take a really long time to crunch through say 1GB of source code if not updated for a few months. Firefox can take an hour or so on its own and LibreOffice is a whopper as well. Older Windows versions, say 2008 R2 can take a good hour some months. NetWare updates need a skilled surgeon (or someone who can read a manual). pfSense (FreeBSD for me) upgrades can be a bit fraught but generally not. However all of those will get you there eventually.
W10 and 2016 are different beasts altogether. They do a pretty decent job of hiding the nitty gritty away from you and I actually like the auto "just do it already" approach and can set "active hours" to tailor the experience. However, it takes bloody ages to run and often needs more than one reboot - sometimes three (ie update, reboot, something doesn't work, reboot, still doesn't work, reboot, now it works).
The error messages you get are awful and generally need forensic analysis elsewhere - a naiive Google will get you to some MS forum and a suggestion to reinstall Windows.
Switching OS is not really a solution but whining about the update experience within potential hearing (HN) of those that might be able to do something about it is a good idea 8)
Though my range of operating systems isn't anything like as wide as yours, but still across a pretty broad range of systems, Windows, especially 10, comes out by far the worst.
My other pet hate on Windows that's been out of control since 7, and getting worse with each generation, is the insane hidden wastage under /Windows that simply constantly grows.
After it's a year old, between winsxs and the various installer and update folders you can easily burn 50-100GB of space under ./Windows for an OS that took say 3GB to install. You can clean up only some of it.
The worst for updates, by far is Windows 10 and server 2016. I'd better qualify that. Gentoo can take a really long time to crunch through say 1GB of source code if not updated for a few months. Firefox can take an hour or so on its own and LibreOffice is a whopper as well. Older Windows versions, say 2008 R2 can take a good hour some months. NetWare updates need a skilled surgeon (or someone who can read a manual). pfSense (FreeBSD for me) upgrades can be a bit fraught but generally not. However all of those will get you there eventually.
W10 and 2016 are different beasts altogether. They do a pretty decent job of hiding the nitty gritty away from you and I actually like the auto "just do it already" approach and can set "active hours" to tailor the experience. However, it takes bloody ages to run and often needs more than one reboot - sometimes three (ie update, reboot, something doesn't work, reboot, still doesn't work, reboot, now it works).
The error messages you get are awful and generally need forensic analysis elsewhere - a naiive Google will get you to some MS forum and a suggestion to reinstall Windows.
Switching OS is not really a solution but whining about the update experience within potential hearing (HN) of those that might be able to do something about it is a good idea 8)