I also have plenty of experience emulating all kinds of things, including Windows - in fact, I have an instance of Win 98 in a VM right now.
That said, I can't agree that it's in any way easy for the average Joe. It's not rocket science, but it's by far harder than just having a working executable.
If nothing else, consider the legality of it - you must have a legal copy of the specific version of Windows, often the specific BIOS, as well. These are not easy (or cheap, often) to acquire these days.
Then you likely need to make sure your CPU supports Hyper-V, then install the entire OS...
Then you often need to make sure you're emulating the specific CPU with the specific GPU, with the specific sound card, or else this specific Windows 95 game will CTD or be missing features. Old games were finicky and OS emulation for gaming is only easy on the surface.