Apple could easily spend a few millions to support some old hackers keeping ancient software alive, they choose not to do it because they either don’t care, don’t know they can do it or don’t think it’s profitable.
You can’t throw all your engineering knowhow out the window just because you’re discussing something politically charged. This is simply how code works.
But emulators are self-contained things. The question is not "should Microsoft support Windows 98 software in a dedicated emulator." The question is whether it's worth the architectural cost of supporting 1998-era software running in your native OS without emulation. I think there's a huge cost to that and I've worked with software developers and Microsoft OS engineers who have long stories about how hard it's been to improve Windows over the past ~30 years, because any major kernel changes would inevitably break some piece of legacy software, and that ruled them all out.
Now obviously things aren't that simple. If all we needed to do was run ~1998 code in 2025, we would of course do it in an emulator. But Windows chose continuity, i.e., they wanted to run 1998-era code in 2000, 2002, 2005 etc. when emulating the whole OS wouldn't have been a good tradeoff at all. It's that continuity that locked them into a straightjacket. My view is that Microsoft's strategy may have served them well in the past, but that tradeoff is no longer worth it.