Re: Why not set an easier goal?
Windows 7, 8, and 10 32 bit can easily run MS-DOS and Windows 3.11 applications. The 64 bit version can't because when in 64 bit mode the processor can't enter Virtual86 mode, because AMD decided so when it designed the x86-64 architecture. Without Virtual86 mode there's no way to run 16 bit applications without emulation or virtualization.
You could still need to run MS-DOS program and 3.11 ones in a VM, because some could have a lot of issue running on actual hardware directly, as some legacy modes could not longer exist.