I’ve also spent my fair share of time in IT. I can’t recall any common issue with the reliability of Windows in the enterprise. Single user issues that originally appeared to be an OS problem later turned out to be caused by hardware. Usually hard disks, though I did find a bad stick of RAM once.

The vast majority of issues I typically saw were application related, usually industry specific software. What I did come to hate was industry applications written to run on the Java Runtime environment. Especially when a user needed several different apps which were not all compatible with a common JRE version. There’s DLL hell, dependency hell, and then there’s JRE hell.