I agree, The lighting would really be a challenge with a ball cap, but I was thinking this: Same setup as you have now, but add an additional light about 15 degrees camera left, just below the subjects eye level and at a much lower power level. The intent would be to maintain the structure on the face but light the eyes just under the brim of the ball cap. The eyes should still be shadowed by the brim of the cap but just visible enough to see.
Please keep in mind, when I make a comment regarding strobist technique, I don't have a clue what I am talking about, just thoughts I have if I were presented with similar situations. I also like seeing your responses on why it would or wouldn't work.
As far as the camo background, I see your point with the digital camo, but the realtree or woodland may be just what you are looking for ---both natural prints of wooded areas but the realtree is a little brighter and a little more detailed.





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