Melissa, your boyfriend's work-in-progress is just beautiful. It really reminds me of Andrew Wyeth (and come to think of it, Annie Proulx paints a bit like Wyeth as well, but in words rather than the brush).
Yes, I can see both those things too!
I have a not-exactly Andrew Wyeth story. Years ago (late 70s?-early 80s?) I was standing in a record store waiting to pay for my purchases. The man in front of me pulled out his credit card, and (without meaning to, honest!) I saw his name on the card "Jamie Wyeth." "Oh, Wyeth," I blurted, "Any relation to Andrew Wyeth?" He gave me what I thought was an unfriendly smile, and said simply, "Yes."
Several years later, I discovered, through reading, that he was a) Andrew Wyeth's son, and b) quite a famous painter himself. I then re-interpreted that moment with him: His irritation with me in retrospect seemed to be about "still in my father's god damned shadow..."