I get into the install-reboot-uninstall-reboot cycle every time I start Windows (yeh, it's broken, but I've tried nuking the upgrade cache, "repeair" etc).

I've also got a few upgrade fails on Linux. Where I had to boot a live-cd/usb and chroot in to fix the problem. And those took a few hours.

I've probably spent more time fixing stuff on Linux. But it you would run a distro like Ubuntu, and not make any customization, then the upgrade experience is much better on Linux then Windows.