Enroute toolpath
Garfield, you may have discovered this feature already, but for a cut like that in Enroute 3, I use the island fill with 3D toolpaths box checked. This would clear the material in the center. The "engrave" toolpath seems to only cut the boundary of the text. Also if the tool is not defined properly as a tapered mill, that could cause issues as well.
PS. please share your surface painting technique. I myself battle with paint bleeding down into the copy. Good luck.