I don't think you are unbelievably dense. You have a good handle on how the wrapping routine works.
In my first post in this thread, I said that it is possible to do it as a wrapped job, though I have not tried it.
I do understand the posters position on this and I do think that Vectric could be better if it were a bit more capable on the full 3D side of things.
It's always a personal choice as to what a person wants to use and do. Therefore, the poster can choose what they want. The poster wants it to operate in a particular manner. I agree with him, and wish the same thing. However what he wants requires some G-Code editing. For some of us that is simple, but for others of us, not so simple. Maybe somday, Vectric will do this sort of thing, maybe not. Again a choice. I do know that the competition to Vectric is FAR more expensive, and not as user friendly.
I also hope that someday Vectric will come up to speed on full 3D machining.
I think though in your last example, maybe the bottom of the pocket is radiused and not flat? That could be an issue.
Imagine the Possibilities of a Creative mind