I once had to start Windows in Rescue Mode and do some weird stuff there just to get Steam back running. It failed to start suddenly and seemingly without cause. For a while (some years ago) I couldn't boot Windows at all until I unplugged a dvd-drive (linux was running fine) - I still use that dvd-drive, windows starts with it again. I bought GTA 4 and couldn't play it because Games for Windows Live wasn't working (still doesn't, but i found the hidden offline-mode). Sometimes I can't delete files in Windows with no cause whatsoever.
At the same time, I'm using a rock-stable Ubuntu LTS with a custom "desktop environment" on the same hardware and never had any real issues i still remember. Oh, thinking a bit longer about it, there were some issues when upgrading to this lts: plymouth didn't stop itself (i had to end it via the rc.local) and pulseaudio didnt work (switched to alsa). That's about it.
Following the herd doesn't lead to an easy life, the herd willingly runs down a cliff.