You can’t just run transport tycoon, rollercoaster tycoon, or xcom without any sort of modification on Windows 10. You’re either using an open source drop-in game engine or a packaged DOSBox setup from Steam. Or in the case of Rollercoaster Tycoon, a rewritten game (RTC Classic).
Windows 10 doesn’t run 16-bit applications, and Windows 10 doesn’t work nicely with a large amount of Windows XP era software.
The fact that I can still run Age of Empires 2 on Windows 10, from 20 years ago, is amazing compared to the backwards compatibility track records of most software.
If only we all got more than ten years to port our stuff forward.
The reason Microsoft killed 16 bit support (In 64 bit editions of Windows) is that very few people were actually running 16 bit apps at that point. Where Microsoft made a decision based on what their users were actually doing, Apple has a made a decision based on what it wants their users to be doing.
The amount of time isn't really relevant. If lots of your users rely on 32 bit software, you should put in the effort to make them work. Apple products are expensive, and I think it's reasonable to expect this in return.
Regular protected mode code has built in support that allows easily running 16 bit apps, so maintaining compatibility was a no-brainer. The moment the trade-off changed, Microsoft decided to drop support for 16 bit apps.
Personally, I don't mind that very much, because dosbox is a great product that bridges the gap perfectly.