I agree with this in general but it can be tough for financial/business/order workflows where an irreversible change may be initiated. From the software perspective an audit log or Git-like history would easily mitigate these concerns but they usually don't exist. And "non-technical" users often just want to "know what buttons to click" to do their job.

To the point of the main article don't think I ever had the opportunity of using Windows 2000. Remember jumping from 98 to XP? Not sure about ME/Millennium either and if it's the same or a variant of 2000.