You have a good point. Most people can't afford to regularly upgrade their MS OS software. Case in point, two jobs ago I was working for a company where we used Windows 95. We never bothered to upgrade because it was expensive and we managed with what we had. Fast forward a few years to where we purchased new hardware that came pre-loaded with XP.
From 95 to XP - it was like using a whole new kind of OS ,everything looked and felt different. My boss (who was barely computer literate) eventually changed back to 95 because she just could not cope with XP.
IMHO using Windows does not teach you to think and to figure things out for yourself. You learn what and where to click but not why so when something is different, something is changed you're a little screwed.