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While I like the image of the "smoky good looks" dude, and the one of couple together, I agree with Chris that the little red-headed boy will be the best subject for you to paint. See if you can shoot a pile of new photos of him to choose from.
The most important thing I learned from the ASOPA conference I attended a few years back is that children's portraiture is two-thirds of the market. I think this subject will be the most likely one to get you additional work.
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