Given a file:
If one re-draws geometry in-between the lines:
Then it may be assigned to a shallow No Offset Contour toolpath with an obtuse V endmill (90 degree was used):
(the insets were simplified down to match the aggregate of each of the colour regions)
and then cut (my apologies, no picture) and painted:
Then, once painted, the V carve proper may be run:
Will, I had to read this through 3 times before I think I understand it (not being a woodworker but always keeping my eyes/mind open…) So the no-offset contour toolpath is to create “boundary moats” around the color areas, which are just surface-painted by hand before the V-carving?
Thank you, Will! That does add materially to the narrative of the workflow. 
All well and good, but I’m thinking that there is an important step missing just before this … masking the painted parts so the V carve can be painted or filled. One wouldn’t want the open V carve for a cutting board.
If you want the V carve to have the natural finish for a decorative piece, but if not I don’t see how one can eliminate the masking.
It’s a sign, not a cutting board.
Will, could you explain the process of creating the line drawing “in-between the lines?” Is this something you did with the off-set tool? Seems like it would only do the outline of the entire object, not one contiguous line that encompasses all the pieces.
I just re-drew things using the Curve tool.
As you can see in the screen grab, it’s multiple pieces, some open, some closed.
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