In my particular case, I stopped upgrading Windows around 7. It is only last year that I decided to upgrade and that was also the year I moved to linux as my main driver. I am not an average user, but I am not kernel contributor either. I am just a guy, who wants some stuff done on a PC I own.
And that might be part of the issue. People need to feel the pain from the devices they have been sold so that they can learn why freedom and ownership is important.