Emulation and virtualization (not technically the same thing, there are key differences, emulators can be virtualizors, but not vice versa) would require resources in order to run efficiently that may or may not be available on the host machine. Plus, depending on how connections are done, it may not be as simple as plug and play to get the guest machine to see the hardware. Not impossible, but may require more effort compared to what most may think it would (if it is beyond a USB connection, it can really be a chore). Bare in mind, if we are talking about 9x era (Win 95/98/98SE), most VM software either doesn't support those outright (anything pre-XP for some) or they have been deprecated at best. Since I use virtualbox, I actually have Vista VM'ed and in the Vista VM use VirtualPC2007 to VM Win 98, because something like virtualbox, 9x support is non existent, but even doing a VM within a VM, it is still flawless (but again, that is the specs of the machine). I would, however, not do that via emulation on the same machine. Performance would be worse.
I'm wanting to say some Summa machines had HPGL support (at least a toggle to enable that support) don't know if that's true or not or still applicable (I've always run Rolands that have said support). Could see about using a generic raw HGPL driver (I think for Windows it's MSPlot or something like that) and just have the machine parse what it needs. Doing that, it's just a matter of setting up the cutter as a "printer" using hpgl and can cut from any vector program at that point. That may or may not be trivial on Windows though. I do that on Linux and it is trivial on that platform, but maybe not so much on Windows. By the time that I was doing that, I was off Windows, so I never tried. Something to think about. Downside to that, is that it does mean that you have to set up things manually on your end and don't get the nice features that apart of dedicated cutter programs. So keep that in mind, that could be a deal breaker. But it may help keep a machine running if need be. Just throwing that out there.