We just had Windows Update brick itself due to a faulty update. The fix required updating them manually while connected to the office network, making them unusable for 2-3 hours. Another issue we’ve had is that Windows appears to be monopolizing virtualization HW acceleration for some memory integrity protection, which made our VMs slow and laggy. Fixing it required a combination of shell commands, settings changes and IT support remotely changing some permission, but the issue also comes back after some updates.
Though I’ve also had quite a lot of Windows problems at home, when I was still using it regularly. Not saying Linux usage has been problem free, but there I can at least fix things. Windows has a tendency to give unusable error messages and make troubleshooting difficult, and even when you figure out what’s wrong you’re at the mercy of Microsoft if you are allowed to change things on your own computer, due to their operating system’s proprietary nature.
Apex with EAC worked perfectly fine on Linux for the last 2 years, EA just decided to break it by replacing EAC with their own anti-cheat which is Windows only.