If there are just a few tears, but no extreme fright on your child's part, I'm good with the idea that you enjoy that picture. If, on the other hand, he is like our granddaughter, who at age 8 still is terribly put off by Santa or any other costumed character, I would say it isn't worth the trauma to the child for a cute picture. We took our two granddaughters to breakfast with Santa at the local senior center this year, after assuring the 8 y.o. that she wouldn't be forced to even get near the guy. She was happy to pose with Mrs. Santa as long as she could stand at a 'safe' distance from him. We were able to get her into a picture with her sister and cousin that included them standing by Santa and her with Mrs. Claus.
I say do what you can to get the pictures you want, but without trauma to the child.