Hey Matt.
You have to create a New Swatch in illustrator.
Make the swatch color - "CutContour" Select a color - i use hot pink, and make sure it's a SPOT color.
outline, or stroke what you want cut in illustrator. then import into caldera, if you did the cutline right, when you open the file, it'll show a sizzors icon on the thumbnail.
drag it to the laxtex icon, then go to setup, there's a contour cut tab, make sure that's checked, and then make sure registration marks is selected as well.
i usually send everything to nest. Then go the the spool and send it to print. After it prints, you can then cut it. By the way, the settings in caldera, override your manual setting on the plotter, so make sure you choose the right pressure and speed in the RIP
good luck.