Well this picture indicates why I find Civil 3D infuriating to work with.

Doesn't Civil 3D know what should make up of a corridor surface? Should it really extend past it's actual geometric constraints? Why does the corridor shrinkwrap stop working if there are crossing boundaries? Why does the corridor surface not work correctly if I don't have a continuous corridor? Can't we have the links, featurelines of the corridor determine the extents of the surface and any triangles outside of it be omitted? If boundaries are required for Civil 3D triangulation why not add both outer boundaries and show boundaries instead of just one outer boundary?
I'm just trying to do a quick study on how to design this trail and having the hardest time doing so because all of these limitations.