If you run a modern distro with a modern filesystem, you can at the very least have automatic snapshots that actually work, and you can restore to a previous state if an update breaks things. The same cannot be said for Windows.
I have booted from snapshots on Ubuntu with ZFS plenty of times and it has worked fine. I've also used Snapper with btrfs and restored from backup and it's worked fine. I've also booted from snapshots in NixOS and it has worked fine. I actually cannot think of a time where any of those examples didn't work fine.