I mean Windows 9x/XP, was this for me: my CD-ROM drive one time stopped working for 3 weeks, then, without doing anything it worked again. Or I had this weird boot error that also over the course of weeks, the boot process would be faster when opening and closing the CD-ROM drive during the Windows splash.

Oh man, or like you edit something in Office or, say Paintshop Pro, and the program just crashes, all data lost. Haha, or you boot and the filesystem is corrupt and you need to run chkdsk or whatever the name was. My god, Windows used to be such a bad operation environment. The worst where Microsoft's world domination tactics, pushing vendor lock to the limit and at the same time making the competion's life so hard that even international courts go to action.

Seriously, computing has become soooooo much become since Windows is not the dominant OS anymore. Many people are so lucky to have never used Windows, others like me might have stopped using it when it refused booting for good. (Becoming sentimental, thinking of my Windows XP/Ubuntu dual boot. The XP just showed a blue screen at some point. After that I stopped using Windows for almost 10 years. :-D)