In the end I did all 7 caricatures in 2 styles; the graphic style below, and the more painted style above. I definitely prefer the style above.
I had to do 7 caricatures. My original plan was to do them all in a clean, simple, graphic style like the image above. It was the fastest way to go, and I didn't have a lot of time.
Here's the rough of this caricature. I did about a dozen of them before I settled on this one.