People do upgrade when they know from experience that their system won't regress. It's not necessarily a Windows LTS ala RHEL what's needed, but something inbet

People do upgrade when they know from experience that their system won't regress. It's not necessarily a Windows LTS ala RHEL what's needed, but something inbetween Windows XP is unsupported and Windows 10 breaks your usage must be possible if MS doesn't want to lose more desktop users. And let's not forget that the heavy desktop users (prosumers, etc.) are those who most of the time are consulted by family and friends for advice regarding computers. So, if you alienate them, there's a high chance they will recommend a Linux desktop for most common computer usage.