Not to counter your point, but I had that new remarkably stupid ":( Oops something went wrong" error popping up the morning I had to give a presentation. I have Windows 10 Home and it forced the updates, failed after an hour, and fucked up the boot partition, removing grub. So just before the presentation, I had to setup grub again and boot into Linux because windows was still stuck with updates. Thankfully my slides were on google drive.
On my office laptop though, Win 10 Pro has been pretty stable.
To get back to the main point, I usually have to spend a day with both Windows and Linux to install everything right from VLC to compilers. IMO setting up needs to be done on every machine, independently of the OS.