Usually cushings horses (that have the long hair as a symptom) do not shed out normally and often retain at least some of the curly hair. That sunken part over the eye does that as a horse gets older and the skin thins and fat pads go away. Janice, GB was very poorly fed before you got him so it will take time to get weight on a guy that old. If he was mostly getting ground corn, even though you started feeding him better rigjt away, it would take awhile for his gut flora to build up to be able to properly digest a healthy diet. The more recent pics, to me, look like he has gained some. I think it was wonderful of you to take him in.
Cherie P.S. If you ever have to sell Stonewall, let me know :)
