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Hi Jeanine,
I just thought I'd throw out a few things here. The most important thing that sets up a painting is the value structure. This is what the eye processes and the brain subjectifies.
That's why squinting helps to clarify both the scene before you as well as your painting.
When I squint, his head all but disappears. The dark values are all clumped at the bottom and the right. The middle tones of the face and back wall merge as well. Therefore, the white of the shirt is what draws the eye.
There is a misconception about just copying what's in front of you, be it reality or a photo. You need to create an arrangement of values that clarifies the important aspects of your composition. Maybe you want to do this with grays first. Start with three grays, a light, dark and middle value on a small board. Then you can expand to more values.
Trying to work out the values in the actual painting is sort of solving the problem after the fact. Painters such as Bouguereau and Gerome did innumerable studies before ever committing to the final canvas. The modern notion of just starting with no plan and working things out on the fly flies in the face of sound traditional picture making.
The best approach is to try to arrange a setup that looks good before you do anything. In the case of a posthumous portrait I would place a replacement model, with similar coloring and facial hair, in the anointed pose and try to set up something that works. It might mean moving things or altering the values (for example, lighter pants?) to come up with something viable. If your value structure works then the rest of the painting will progress more smoothly.
I would try to isolate the head first off. What surrounding value(s) would best set it off? Once you arrive at this expand outward. What Value clothing and props would best emphasize him. Do you want to feature his head? His torso? His whole body? These type of questions will determine the best course of action.
Have fun!
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