I'm currently cutting directly from Corel Draw with Windows XP. So if I buy Cutstudio I should be able to cut from that?
CutStudio is really a strip down cutting program. If you are cutting from CorelDraw already, I would just stick with that versus CutStudio.
The other option (and I stopped using Windows before I got around to see how easy or even possible) would be to try to setup your cutter as a printer, but use the raw HPGL protocol (I say RAW, because that would send all info and it would be up to your plotter/cutter to parse what it needs and leave the rest) and then just use the print function of your program of choice and go from there. This is how I handle my cutters on Linux and cut from my Linux programs as there are no OEM drivers to help this process along on Linux. HPGL protocol is supported on Windows, but it just depends on how easy it is for a user to set up that protocol for a virtual printer. Exceptionally easy on Linux, but that's a whole different animal compared to Windows.
Virtualization is a way to run one physical machine, but running 2 OSs at the same time. It has it's drawbacks, but I do like my VMs, but you must properly spec out your physical computer to be able to handle running a VM. What specs your computer has can directly affect how good the experience is. I wouldn't get a budget computer and try to VM from that and expect great performance. Depending on the specs, it may work, but more then likely with a budget rig it will be very, very slow.