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Try the impossible
The range of values in nature far exceeds the range of values available in paint, so your basic premise is flawed. You need to establish certain givens (such as an accent value in the shadow) and then estimate up from there.
Once you establish certain values this way, you can compare other values in relationship to the first one.
For example if the skin shadow average is 3 values lighter than the accent and the flesh in the light is 4 values lighter still, you would ask yourself, "where is the background value in relationship to the skin in the light and in the shadow?"
The object is to ratio the values in the scene before you so that they can be painted within the range available between black and white pigment.
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