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If I had to pick from these I would choose #3.
The problems you will have to confront are these:
1- As with all outdoor photos taken in the direct sun you get a flattening of the values across the board. This really kills you when you are trying to create form in the facial features. One way to mitigate this is by working large.
2- If you paint this exact composition on a 36" tall canvas your head size will only be 5.25". This is getting toward the minimum, certainly not large. When you combine this small head with the problems of not having a lot of value shift in the features you are beginning to meet some real challenges.
3- I don't know what type of camera you were using, but if it is something like a 5mp point and shoot type, you will not see much detail at all in the eyes or in the hands when you enlarge this photo. Even with a really great SLR it would be hard to extract much detail.
If you place these challenges in the hands of a really experienced painter this could end up being a fine painting. For us mortals it could be a real head knocker. My advice would be to keep the entire image loose and suggestive rather than trying to work a fine line. The background could be a real asset to that end. Keep your strokes broad and don't be timid with the paint. This is not easy when you're trying to capture a likeness.
This would be my approach.
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Mike McCarty
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