for me Windows is the king in backwards compatibility. I get the sense they expend significant resources doing testing in this space and scrutinizing ABIs and APIs and all that. They don't want to disturb the developer ecosystems with bedrock changes.
ah what a conundrum, pitting legacy over security that's a big tradeoff decision. Those mostly seems like independent topics but I wonder if the deeper you go in maximizing legacy support the more vulnerable you make your systems in falling for security lapses of some kind. I wonder if these two things tangle in unforeseen ways deep beneath the surface.
Definitely, MacOS busts kext extensions and other software without mercy leaving the devs to either keep up or to bite the bullet and abandon ship. For projects that are labors of love those often fall to the wayside and you get stuck romanticizing earlier versions of MacOS when you used to be able to do xyz. One I’ve been longing for is a rerelease of https://www.orderedbytes.com/controllermate/