I have applications and games from the 90s that still work in Windows 10. The idea that developers have have to constantly push updates is unproductive in my opinion.
the real things that were dropped since then were 32 bit protected mode apps, and for such you have plenty options for both virtualizing and paravirtualizing.
I can boot basically any other version of Windows under my windows system using Microsoft provided software.
I can even just go boot up older version of Windows on current hardware if needed be, up to a point.
almost everything from eighties to today I am able to run one way another, nothing "stopped" working.
Apple physically removes old software from their delivery platform or signing servers and if you lose your devices it's lost forever
how does it even compare?