Hi Thirsty -
When viewing the oeuvre of Zuckerman and reading discussions of his technique, one thing stands out to me: His best known images always use lighting techniques which tremendously reduce shadows in the subject, specifically shadows cast by one part of the subject on a different area in the subject (self-shadowing). In addition, he just about always blows out his backgrounds with other dedicated lights.
Some examples of this can be seen here:
http://www.thefstopmag.com/wp-content/uploads/080121ss_andrew_wyeth_00077.jpg
http://cdn.creativejournal.com/images/attachments/000/003/872/main.png?1368171595
https://s-media-cache-ak0.pinimg.com/736x/6e/33/70/6e33705d88c28727365791ec40333ed3.jpg
One of his favorite lighting configurations to reduce self-shadowing is a beauty dish directly above the camera and a ring light below:
http://jcowiephoto.blogspot.com/2010/09/quest-for-light-andrew-zuckerman.html
Unfortunately, IMHO, if one does not start with an image lit as described above, it's going to be impossible to re-create his signature "look", using only post-processing of normally lit subjects.
OTOH, if one does not have the same lighting equipment as he uses, one can get reasonably close using a simple, inexpensive light tent, e.g.,
http://www.boostyourphotography.com/2014/03/light-tent.html .
Of course, the difference is that in his typical setup, the light is coming from the front of the subject, whereas in a light tent, one typically has to leave the side facing the camera open (so the camera can see the subject) this means that in a light tent, the light is coming from all sides of the tent, EXCEPT from the front, so it's not perfect.
Post-processing can maybe get one a bit closer to Zuckerman's "look" by enhancing detail to compensate for the flat lighting, e.g., by reducing the lowest spatial frequencies in the image using SW such as Topaz Adjust and Topaz Detail.
Just my $0.02,
Tom M
PS - In your 2nd post, you described the look of the example image as pencil-crayon-like. To be honest, I wouldn't describe his signature look in those terms. Rather, I think you are just seeing the lack of self-shadowing.