What communication port is it using? That makes running a VM a little bit more troublesome if it is say a serial port versus USB that the cutter is using. Not impossible, but definitely not plug and play as much as a USB one.
I love my VMs, they are great for this very reason, but they have caveats with them. Can your new rig handle running a VM and still handle your other day to day activities if you have to multi-task during that 5% cutting?
To do a VM legitly, you'll have to have purchased your copy of the OS to activate (non OEM version unless you are using the hardware that is bound to that OEM activation number (which would probably be doubtful)). Win 7 Pro and higher did allow one to get a free XP VM and use VirtualPC, but I don't believe that free option is available, nor is VirtualPC around, it's been replaced with Hyper-V or something like that. Could use VirtualBox (certainly better then VMPlayer, other one that I would suggest is Workstation Player (commercial version from OEM that supplies VMPlayer).
If there is a way (I left Windows (and Mac)) long ago, but if there is a way to setup your cutter as a generic printer that uses raw HPGL on Windows, you could use almost any design software and "print" (cut) from that. Exceptionally easy to do in Linux via GUI, but I never had to deal with that when I was on Windows, so that may not even be an option on Windows, I doubt very easy. But using that method, could even use Inkscape on it and it'll cut directly from there without any drivers. At least, I'm able to do that for my Roland GX24s on Linux, again, may not be an option on Windows. Just throwing that out there as maybe a possibility of looking into anyway.