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Hi Dave,
I, too, am very impressed by your portrait. I think you did a great job. It's especially difficult doing a posthumous portrait from reference photos that you did not take yourself, and may not have been taken in lighting that works well for a painting.
I agree with Kim, and I wanted to add that color would be an important aspect to work on simultaneously with edges. The color in the shadows relates directly to the background, because the background is really the space around the figure. If you had used a greyed midtone, for instance, it would follow that the shadow side of the skin, clothing, hair, etc., would all have some of this greyed midtone in them. In your painting, the blue of the shirt in shadow is very blue; the orange of the skin in shadow is very orange. If you had some orange in the blue, the shirt would be more shadowy. If the orange of the skin had some blue in it, it would be more shadowy. Tied in with this, if there were both orange and blue in the background, the complementary colors would grey the background, make it "airy," unify the color scheme and make the figure sit in the space.
This is just a simplistic explanation; there are a lot more subtleties to be explored and a lot more possible solutions, but I am confident that you will "get it." In relation to what Kim was saying about edges, when you have similar colors in the background and the shadow side, this makes it possible to soften the edges on that side so that the form "turns" into shadow.
Alex
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