One of the things which can be difficult to grasp is what will be cut and how when one first makes toolpaths. If you select one path, or multiple paths which are not nested, either their perimeter or their interior will be cut out. If one selects multiple paths which are nested (say a border and a piece of text within it), then the pocket will begin at the outermost path and leave the interior paths uncut as islands.
Another concern is that some poorly constructed fonts or drawn path geometry have the incorrect winding (outermost path starts as clockwise, not counter-clockwise) which will prevent Carbide Create from generating and/or previewing a toolpath.
Also, Carbide Create doesn’t have a full suite of endmills defined, so one has to set up a V-bit if one wishes to do any V-carving.
In addition to the videos we’ve got a formal user guide:
http://carbide3d.com/carbidecreate/userguide
and there have been a few additional tutorials worked up by the community which ought to address what you’re having difficulty with. Please see:
and
as well as Inlay Work (Woodworking) - #2 by WillAdams and Inlay Work (Woodworking) - #25 by WillAdams
I’ve been working on an addendum to the manual at: Shapeoko CNC Router, Rigid, Accurate, Reliable, and Affordable — I’ll see what I can work up there about regions and toolpaths.