Ouch. That sounds like it sucked, big time.
My worst story regarding Windows is one of my first experiences with Win10. I had gotten a mini-PC, passively cooled and tiny, to connect to my NAS and stream my library via Kodi to my TV. It worked perfectly immediately at boot, wouldn't ya know.
But wait! Windows update wants to battle!
Three hours and many reboots later it comes back to the login screen. Seems fine, so I log in. SCREEN FLICKERING
I can hardly navigate because of the jumping display and the distortions from my TV trying to keep up. I figure it's drivers, so I reboot into Safe Mode, which I find out is stupidly hard to figure out if you don't know how to already (and even if you don't have a constantly flickering screen). Turns out that Safe Mode with Networking is bogus and doesn't work. Yay. At least Safe Mode doesn't flicker, so I copy the information and check on my regular PC. Download some drivers and a couple of helper programs (don't remember which ones, except Intel's driver update helper). Nothing works. Fuck all happens.
Three days go by. I try absolutely everything I can think of, while the screen flickers, giving me a daily headache. Yay again.
Finally I land in a menu I didn't think I'd ever have to enter. I am not completely sure where I am, because I have a splitting headache and can hardly see the screen, but I manage to find a dropdown menu and it fixes everything.
It turns out that Windows 10 is so retarded that it tried to force an update frequency on my TV that it doesn't have. It was set to 55Hz. My TV only has 50 or 60Hz, and I'd figure a fucking OS would be able to automatically discern what works. It's an LG, so it's not like it's a noname brand or anything either. Fucking Microsoft, man.