One of my coworker that uses a Mac has an issue with a USB dongle that stopped working randomly, not even with a system update. If he uses on its laptop the external monitor remains blank, the same dongle with another monitor and another identical Macbook with the same macOS version works, the same dongle with the same PC and another brand of monitor works, the same PC with the same monitor and a dongle of a different brand does work, but a different dongle of the same model doesn't. So I guess for some reason macOS saved the ID of that dongle and the setting got corrupted. Tried to reset the hell of it and it doesn't work.
I've never had similar issues with Linux. Most of the time when something doesn't work with Linux you just look at the logs, figure out what is wrong, correct it, and it start work fine again. Configuration of the system is predictable, if you install a software and then you uninstall it the system is left in the same state as before installing it, it doesn't leave files that waste disk space, as well as when you upgrade the system (yes, every Windows or macOS update leaves old stuff behind that it's impossible to delete, effectively "leaking" disk space at the point you have to perform a clean install).