It's not hard to do either, especially on Windows where backwards-compatibility is almost completely guaranteed.
Of course those in the planned obsolescence mindset would fight hard against it, because then it would be harder for us to take the good without the bad.
I think it's more like your gen1 wi-fi enabled Philips screwdriver stops working because it's EOL as opposed to because nobody uses Philps screws anymore. Sometimes it's the latter, but not always.
A more direct analogy is right there; your Phillips head screws cam out more easily than Torx. Everyone who wants screws that don't shred as easily moves to that weird 6 pointed star pattern, and your Phillips head screwdrivers are suddenly EOL'd.
Of course those in the planned obsolescence mindset would fight hard against it, because then it would be harder for us to take the good without the bad.