I've never, ever had the severe kinds of problems you mention, and I've been on Ubuntu or its derivatives (most recently Mint) for years and years.
I've seen all sorts of similar stuff. Mind you, it's not as bad as the GP suggests. If you're running Debian testing, you *will* get bit on the ass inevitably. And Ubuntu prompts you to boot more than any other distro largely because the others don't really prompt you to boot at the GUI layer after a kernel update.
I've seen some updates that render a system unbootable (the one that comes to mind was that /dev/hd* to /dev/sd* migration a while back), and there's been some pretty boneheaded small glitches too (Ubuntu recently updated to show a pretty background image at boot rather than the far more useful prompt for my whole-disk decryption password). And things like drivers can be a pain (nvidia graphics and anything involving the name "Broadcom" in particular).
The main difference from Windows, though, is that I've never, *ever* had to solve a Linux distro issue by reformatting. I've had to boot into rescue to edit files, sure, but in over 20 years of running Linux, I've never had to completely nuke a system in order to "save it" from a broken update. In fact, I think the only time I've had to do so was way back when I had to tweak my own storage drivers.