Loosie, he is in no way out of shape. His trainer (from the racing days) told me he is in as good a shape or better then during his racing days, he's been teasing me and asking if I wouldn't let him run just one last time. (No way!) The weight he gained is 90% muscle, dude is strong! The pictures pasted into the thread are from June, I'd only had him for 6 weeks at that time. If it works this picture is from October, it shows he's more bulky then he was. Starship trot on Flickr - Photo Sharing!
Don't know how to post the pictures in here, link will have to do.
As a racehorse he is used to being prodded and he does have a high tolerance for pain. So you are probably correct, unless it is acute and I have the exact spot he'll not react in a way that indicates pain.
In the near future he'll get new shoes and if that doesn't do it I'll have the chiropractor come out to have a look at him.
We'll just keep trying different things as it is a horrible idea to me that I may be causing him pain, however he is very smart, completely has me in his back pocket and he might just be messing with me.
We'll figure it out eventually.