I've made some progress. I learned how to import a real airfoil with a non-zero thickness trailing edge (NACA 0006) and loft it into a simple fin shape. Then I used the technique in the video to make a fillet. It's pretty good and I'm going to close this thread. Thanks for the help cotty!
Fin fillet ala Curviloft.png
Fillet 2(v6).skp