IMHO, its convoluted, but driven by the agendas in hitech toward neurological programming.
Some of the problems with the MS SW is simply very poor documentation. Microsoft always had a problem with keeping their operating system Basis of Design so tightly chested that one corner of the company didn't know what the other was doing. People migrated to what they could engineer and manage, hence their new SW rollout and imaging programs. If you don't know what it does, just copy and paste it into a backwards compatible machine and hopefully it works.
Some people want to meet milestones, others believe its bit too arrogant.
We seem to be living in a Plug and Play, replace the part world, where nobody knows how anything works from the bottom up, anymore. Installing the OS is fraught with steps to perform, but few are really following what is being performed systemically.
If it were money driven, MS wouldn't care who was getting it, they still would have their hands in the transaction at activation. IMHO, it's so complicated, they're just trying to shut off their older systems and keep their hands in the cookie jar on the new ones.
IMHO, I tend to think it's more about security risk mitigation. We're at the brink of another revolution with IoT. There's going to be magnitude of order increases in the number of processors connected to the internet, and a commensurate rise in the potential damage they can do if they get owned by the 'bot herders.