You can make an old school DOS rip of the image. Or you can put the image on a USB stick and boot from a Gotek or similar.

The obvious problem with running an image from DOS is that it will take over the entire memory and overwrite DOS and the calling program. Does DOS even allow this?

Well one thing I notice is that booter .IMG files typically won't open in WinIMG. If the Gotek is the only solution I might stick to my floppies as long as I can unless they come out with an external one that can connect to printer/prll port.

WinImage uses the old RAWRITE format I believe. DOS booter disks use their own exotic formats which WinImage won't recognize.

There is at least one way to simulate booting a floppy disk image from DOS: http://www.oldskool.org/pc/flopper

Not all booter games are compatible with it, though, and you may have to restart the system to get back to DOS.

Sadly Flopper requires a 386 which is already too fast for many Booter era games. So do Goteks have no issue with these much older booter images, then? Seems like the only long term solution.