Extending the trial is no problem- just email me when it shuts down.
For your part, the roughing does not appear to be necessary. The waterline passes will follow the exact contour of the part and let you stepdown a reasonable amount to keep from overloading your cutter/machine. The pencil pass will do a final full-depth cut for anything remaining.
The terminology used above mat be a little different than a traditional 2D CAM program but I suspect that the finished toolpath will be reasonably efficient and require very little effort on your part.
As for why the roughing takes two passes, it's trying to remove a volume of material defined by the part boundary and the area to be machined. It will try to remove all material between the two of them. You are only looking for the part boundary to be cut so roughing is the wrong strategy for this particular application.
-Robert
(Note: The opinions expressed in this post are my own and are not necessarily those of CNCzone and its management)