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I paint fallen soldiers for families, so I do a lot of work from photos since my subjects are no longer here. Working from photos is very difficult for reasons mentioned in the comments, above. One thing that seems to help me is to enlarge the head to around 8 inches (more or less), and place it several feet away. It isn't perfect, but accomplishes some of the things previously mentioned in this thread . . . softens contrast, generalizes. I also scan in the photos from which I'm working and tweak them in Photoshop. It's not perfect by any means, but it helps make it look less photolike.
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