CorelDRAW with some cutter plugin software is my suggestion.
CoCut for that model seems supported. This would probably be the easiest method that I'm aware of. Might cost more then wanting to spend initially, but probably the least hassle prone.
I think the
official driver support has stopped with Win 8 (at least at this time) so that makes it harder to use just plain ole File>Print in graphics program of choice, so going to need some type of program with a built in driver for the easiest solution.
Only other method is to manually setup a print driver to allow for "printing" to the cutter. Easy enough to do in Linux when using my Roland's, but I don't know how easy it is on the Win side of things (since my version of legacy Windows are in VMs that adds an extra layer that I don't want (or need) to deal with, so I've never bothered with seeing how easy it would be with Windows to do that).