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I am still very much interested in hearing more opinions on just how delineated/sharp the line should be where the shadow meets the light. I suppose it also depends on the mood I want to convey. And like so much, there is probably no magic answer.
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Exactly. It depends on the subject and the mood you want. Look at paintings you like and see how they did it.
Remember, though, that when you set up a model in the light you think would be just right, it will usually turn out to be too contrasty in the photograph. That's what cameras do, whether film or digital. They increase contrast, sometimes by a huge amount.
A simple tip when shooting by window light (which is the easiest way to start in any case): In order to increase contrast between the lit and unlit sides of the face just move the subject closer to the window, to decrease contrast move him or her away from the window.