[thenonsequitur]

"If Windows were equally messed up as Linux I'd expect to run into the problems at around the same rate."

My personal experience (as someone who has been dual-booting Windows and Ubuntu for nearly a decade and uses both operating systems regularly) is that both have a lot of annoying problems, but Windows has always been way more of a pain in the ass, and I've run into more problems using it. Especially when it comes to driver issues, Windows has problems (it took hours to get a standard WiFi card to work, and once my video driver got corrupted so badly the system wouldn't even let my try to fix it, and restore failed -- I had to reinstall the OS to fix it).