Debra,
Yes, I get the same feeling of archetypical 60's hippy guy: almost as though he's somebody I knew. So, you've definitely captured that aspect of the subject. In fact, I did know somebody, Larry Miller, who strongly resembled this man. It took me a minute to figure out who it was. Larry wore granny glasses, so that threw me off until I squinted at the image just now.
The view definitely appears to be from below, so the smaller than usual forehead would make sense due to slight foreshortening. The beard also adds to the effect. Queen of chins, it figures.
In the rest of your post you're getting a little outside my usual idiom. I think you've every reason to be confident in your artistic skills. I think you're quite talented already, and certain to become more so. But I'm not sure I understand all your concerns. Help, I need help here too. Where's Mike McCarty when you really need him?
