He’s lovely. I wish you the best. 
Yes, he might be due to get another adjustment if his back shape has changed in the last few months. I am very hopeful his current way of going is just due to a lack of strength, but am getting the vet out this week just to ensure there isn’t anything obvious on his back, feet, stifles, etc. that might be causing it to be worse.
Thank you! He has such a big, goofy personality, and has been a joy to have!
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I wouldn’t be asling a 3 yo (Off Track or otherwise) to do that. I’d be working on long and low, with transitions to build strength.
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He is four now! But nonetheless, still very young. We do lots of transitions and start off sessions with a lot of long and low work in the walk and trot. It is difficult to do this in the canter. Unless we go off property and have a large area to canter around in where I can allow him to really move around more freely, I’ve been limiting the canter to a circle or two at a time and also do lots of transition work in the canter as well. A few folks on here have said working him straight is going to be more beneficial than staying on a circle, though, so I am going to try that!
I don’t really think so. There are many saddles with what I call a “cathedral pommel”. My OTTB mare has withers like this, and Prestige, County, and Amerigo all fit her
I found a used County that is working well for him!
Well okay. Bottom line is that if the saddle is to sit behind the shoulder blades. The developing blades and width of the horse a properly fitted saddle is key. You can’t just sit any saddle on that upswept wither and flat back and expect he won’t protest. No matter if the width is perfect. Obviously the Op has addressed this. It was just a thought. Trying to help.
Yes, that’s the whole premise of saddle fitting - fit the lateral and longitudinal shapes and widths, AND make sure the pommel properly clears the withers. Too many people get the rest of it right, see a low pommel, and put a front shim on, which then un-fits the entire saddle
The same issue goes for mutton withers. Withers are part of the while fit system, not just the back shape and lateral width and shape. Lots of saddles fit horses like this 
Again. I said a challenge. Not impossible. Just something to be addressed. That is all.
I didn’t read all the comments but I knew a horse that had a lot of the same behaviours (curling BTB, kicking out/bucking in the canter) and the problem was her hocks.
