Hello ReNae,
Just one thing that struck me right away; the right eye ( on our left) seems to be displaced. In the photo her eyes appear to be the classical one eye width apart, whereas in the painting the interocular distance seems to be greater than this. It makes her look a bit like Jackie Kennedy in the painting compared to the photo. Since the eye location on the other side is pretty much locked in between the nose and the edge of the head, maybe you should try moving the right eye inboard so the inner corners of the eyes are about one eye width apart. Maybe you've already spotted this in the overlay process.
Another thing about that eye is that in the photo the upper lid makes a sharp descent as it approaches the inner corner; it's a slight departure that gives character to her face, and is something you might want to catch.
Finally, the heights of the eyes relative to the widths could be expanded slightly for a more youthful appearance.
I'm a little hesitant to offer these suggestions since I'm pretty inexperienced, but at least they're fairly specific so you can see if they make sense without too much effort.
Looking forward to seeing your progress on this one!