I will get some pictures of just his back and shoulders tomorrow in the afternoon when the lighting is better so you guys can see what he looks like without a saddle on and then a few with the saddle again.
TinyLiny- Could you post a pic of your saddle? Just curious about the gusseted panels.(I'm still kinda a noob about english saddles/fitting lol) Also how exactly can you tell a saddle is made for a warmblood? Certain sizing, brands, or builds of the saddle?
A pad with shims sounds like a good idea in theory but, the way it rocks most of my weight will still be centered in the middle-front of the saddle instead of even pressure throughout. Not sure enough padding will "fix" it. :/
Thanks everyone for your opinions and sharing your knowledge!