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Natalie,
Thank you for considering my post. At the risk of sounding evasive, I would not set this up for a painting. For photography it works much better. The reason I say this is that the color, as far as temperature, is muttled. If you look at the background, my conclusion is more readily understood.
The cast shadow to the right of the boy's head is a relatively warm one. This means that the light source is to the left and a predominantly cool one (most likely the blue sky). If you look closely to the left of the boy's head, you will see a weaker cool shadow. This indicates a less intense, more distant light which is distinctly warm in temperature (likely a lamp light). I also get the impression that the light to the left is also more diffused and the one from the right is more sharp.
Both light sources, opposing in temperature, altering in intensity and edge being allowed to shine on the same area (the cheek on the right) is a nightmare for painting. It of course can be done, but why bother.
Some of the ways one can solve this may be to ignore one of the light sources and just paint the effect of the other (a lot of guesswork). One could also reduce the effect of the color temperature of one of the light sources and thereby make a cleaner color statement. (still the problem of the value change from light to shadow is unaddressed and the shadow-side temperature is weak). Another (more popular) solution is to ignore all decision making and just copy the photo with no regard to color and repeat all the problems from the reference into the painting.
As I started out with, it makes a better photograph than a reference for a painting. This was the long explanation (and correct one for me). All that said, I think your decisions in the first version were better. The exception is that the center of the forehead is in light. I would make the shadow from about the right of center of the eyebrow on the right and moving up and to the right until it meets the hairline. The other areas were well thought out and your work to find them is to be commended.
The clean decision of light and shadow in a painting is a valuable key to the reading of the design and therefore strengthens the composition. It also give one a great deal of freedom when painting for effect when one is faced with the inevitable problems, working from life, namely colors which are simply outside of our range of pigments. It is similar to the idea that music can be transposed into different keys and ranges but usually with sacrifice of one sort or another. Paintings must be transposed into different keys and ranges in order to obtain certain effects but usually with some sacrifice. If one understands the role of a strong grasp of light and shadow being opposing forces, then their relationship can be moved around the value and color scales and still maintain a near perfect representation of your subject. A muttled intermediate zone is a fly-in-the-ointment and often destroys an effect.
This zone is usually the darkest part of the light and can be more easily grasped if one casts a shadow onto the subject and moves it around. If movement is seen, then the area is in light. If not, it is shadow. After all a shadow cannot be cast into a shadow.
I hope this is helpful and not more confusing. I know it makes perfect sense to me as I write this but may not to others. If I have created confusion, my apologies and please post again.
Clayton
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