I second the recommendation to learn the Gradient Mesh. I'm going to try to teach myself the mesh tool this winter, since I've seen how incredible the results can be. I hadn't initially noticed the "looping" in the portrait, but now I see it. It's something that you can overcome with practice, though it's frustrating at first for sure!
If you need inspiration, you can check out
www.lifeinvector.com
I go to that site frequently just to remind myself what CAN be done with illustrator and try to glean what information I can from looking at the illustration portfolio.