Please see Shapeoko CNC Router, Rigid, Accurate, Reliable, and Affordable for a guide which should help you find your way — see Shapeoko CNC Router, Rigid, Accurate, Reliable, and Affordable if any terms are unfamiliar.
Belike Illustrator is part of your problem, since it allows one to develop bad habits doing Bézier curves — unfortunately Silicon Publishing seems to have withdrawn their macro for directly creating G-code from w/in InDesign.
I really believe that you need to just grasp some basic terminology and learn to understand the difference between pocketing and profiles and that it’s pretty rare to need to follow an outline path for text.
You may find this discussion of interest: