I have had many many saddle woes with Cinny since I got him. It took me over 20 tries to get a dressage saddle that he would work in. I have gone over 30 with Western. I had two really good trainers help me fit him with saddles only to have him buck up and down the arena as if he were constantly stung by bumble bees. I had a pro saddle fitter come out and the saddle he fitted him with that should have been a good fit, made him buck like a pro bronc on the lunge line for 15 minutes straight....only stopping because he was literally so exhausted he was ready to drop.
My friend Katie's saddle fits him pretty well, and we have been able to work him in that. I found one that looked like it would fit similarly but alas, the tree is a touch wide and technically, it doesn't fit because there isn't enough clearance over his withers, we only have 2 inches versus 4. HOWEVER....he actually likes it. I put a decent pad under it and took him for a spin and he worked wonderfully in it. No gritting teeth (his habit when he's irritated), no head tossing, and his gaits were perfect as if we had my dressage on him. He even gave nice bends which he doesn't do in my friends saddle.
So my question is, if Cinny likes and works well in this saddle that technically doesn't fit right, is it really that bad to keep working in it versus one that technically fits but he hates and trys to buck off??