https://github.com/otya128/winevdm

This is a little tool I found the other day that lets you use old 16 bit applications on a modern 64 bit version of Windows. You extract it to a directory, and then there are some installation files you can use to set it up. It gives you the choice to have a console window that your old program of choice will execute inside of, or you can have it run without that extra window.

So far, I tested this with the Windows 3.1 version of Chip’s Challenge and several Klik & Play games. They took a minute to start up, but both of them ran fine. I can’t guarantee it will run your favorite 16 bit games, but it’s worth a try if you grew up on this kind of thing like I did

Wow, this sounds really handy. It could help fill a big part of the annoying gap between "stuff that Dosbox handles" and "stuff that newer Windows versions can run with Compatibility Mode".

It’s definitely easier to set up and use than it would be to make a DOSbox/Win3.1 setup. It’s a hell of a lot more convenient for just playing crummy old Klik & Play games than the whole DOSbox thing would be, although I haven’t tested its compatibility with that sort of thing very much