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Clayton,
I have read this post very carefully and tried to absorb what I deem to be years of wisdom talking. I must say, I still have a questions, though.
I know that art can't be "mathematized" into one single set of rules or explanations that are right and all others are wrong, but I was still intrigued by your statement that a plane is either in shadow or in light and nothing in between. Even if others may have reasons for saying otherwise, I am certain you must have a very good reason for saying what you said.
I chose the following photo to illustrate my question because the boy's face is very smooth and the gradation between light and shadow is certainly a slow one.
I was curious how you would treat this face when interpreting through your eye what is light and what is shadow. I've drawn to hypothetical "boundary lines" where I think the light ends and the shadow begins, focusing mainly on the shadow side of the face and changing the cheek width.
But I'm unclear where you might draw these lines. (If neither is what you'd do and you'd like to be able to tweak my file instead of starting over, I'd be happy to email the original Adobe Illustrator file).
Anyway, if your eye interprets something very specific when you make your actual dividing line between shadow and light, please explain a little more why this makes you feel like you paint better than when you think in terms of light, midtone, and shadow.
Thanks for sharing your wisdom.
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