When a Linux update fails (which can happen automatically; for example, Ubuntu 16 reserved a very small boot partition and upgrading it to the latest version leaves it with too little space to keep the normal amount of kernels available), you end up digging through files and configuration and terminal commands. This is different from Windows where you have four buttons to click, and if all of those fail, you either reinstall the entire OS or reverse engineer Microsoft's logic and directory structures.
When Windows fails, the OS usually detects the issue and reverts all the work. Their self repair is excellent. Sure, Windows Update may be broken for a while and the forced restarts make the whole process annoying, but the system still works.
Linux can easily leave the system unbootable while Windows has the necessary recovery options. Boot recovery and System Restore are some features that definitely improve Windows' stability. Timeshift with a CoW filesystem and some GRUB hooks can somewhat replicate the effect, but I haven't seen any distros enable all of those by default yet.
For example: I enabled encryption in the installers of both Ubuntu and Manjaro and hibernation simply didn't work. I managed to make it work with some config tweaks on both, but out of the box my laptop simply shut down and lost all of my work when the battery got low. My laptop also had no sound, stuttery video and no working microphone because of missing drivers for Nvidia, Intel and Realtek chips. Udev rules broke sound every time I unplugged my HDMI drive or let it go to sleep.
Windows sometimes breaks down because of shitty drivers, but I've never seen it happen this severely.
This was probably all related to the manufacturer's decisions about board configuration, drivers, and other proprietary crap, but the end user doesn't care whose fault that is and neither should they.
