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Leaving your questions for Karin to her, I would just suggest that getting a "9" value in this kind of light likely has much more to do with photography than reality. (For the same reason, I think the nostrils are too dark in your painting -- a very common error, by the way.)
"Stripes", as you called them, of value aren't necessarily suspect -- IF you're trying to convey dramatic changes in facial planes. If you're not, then you of course have to work on the transition, but first make sure your perceptions about how dark the darker values look are correct. If you wind up lightening them, your problem with "stripes" may well resolve itself.
Finally, the urge to push the shadow side into a very dark range might have as much to do with the fact that you've not yet brought the lighted side of the face "into the light". If you squint at the painted face, it has nearly a monochromatic and limited-value-range appearance.
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