Question how to automate cutting paths on a vector image

You can do this with actions and using offset path instead of setting a stroke weight as the stroke weight have to be setup individually, whereas offset path will add a new same color object behind the original to provide the bleed. Not exactly what you were asking for, but a work around. See my attached screen shot for how they should be setup. Here are the actual steps.

If not familiar with actions-->
Select Window -> Actions
Name it whatever you want. You can also assign a Fkey so that you can run it from there.
On the bottom click on the symbol to the left of the delete bin to Create a new action
A new action will be created and will begin recording. So anything you do from this point on until you hit stop will be recorded.
ctrl+a (select all)
ctrl+c (copy)
Select Object -> Path -> Offset Path (settings I used were Offset: 0.05 in; Miter Limit: 4; Line Joint: Miter
ctrl+shift+a (deselect all) Make sure to use keyboard shortcut or the Select -> deselect all from the top menus to deselect. Just clicking on an empty space to deselect won't work).
ctrl+f (paste in front)
In the Pathfinder window click on Unite (also known as weld)
In your Roland VersaWorks swatch window select your CutContour swatch.
On the bottom of the Actions window, hit the Stop button. (last on the left)

I broke it down as if you were a complete beginner with Illustrator only because I obviously have no idea what your experience with it is and so that it is as easy as possible. I don't mean any offence to it lol.

 

I probably wouldn’t even do an action for that, takes about 30 seconds. The results will be quicker but you’ll still likely have to go in and screw around with the nodes on some joins