Aaron,Firstly, we just need to clarify that the product you are trying to install is "Stardraw AV 2007" (not SmartDraw).
I can confirm that with VMWare, you are able to virtualize a USB device and that Stardraw is able to recognize this when running inside a VM.
To be clear, the USB key should be plugged into the physical host machine and your VM configuration running on that physical machine should be set so that it maps the physical USB port on that host machine to the VM.
No special configuration is needed of Stardraw.