I've been told flat-out not to even attempt "A" circuit hunters because the judges won't mark us up good, specifically due to his appearance. But I find it really hard to believe that if we throw in a really good round, we still wouldn't place due to appearance. However, my goal is still to get to the "A" circuit and place, even if in 6th, just to get rid of that thought completely..

To be honest, he's really out of shape. He's on 16% roundbale about 12 hours a day, plus gets grain so he chubs up, but unfortunately the barn is so far away that I can only get out on weekends (if I'm not working!) so he usually gets to relax and get fat 6 days a week, and then I go up and (oh dear!) work him. Not the best combination, however we're moving at the end of the month to a barn 20 minutes from my house and we're going to start into a training regime and hit some schooling shows this summer.

As for jumping, we've dabbled up to 2' because we fell back on training time and eventually I just stopped because we needed to get out flatwork 100%. He's normally really good but still has those baby moments where he thinks he's into formula one racing, and a nice controlled canter isn't in his vocabulary! But he snaps his knees up nicely over fences and absolutely loves jumping. I'm still on the fence with disciplines with him as he's not really telling me what he enjoys except for jumping. [If you set up a random crossrail in the arena and let him loose, he'd head for it and pop right over it]. So that's why I figured I'd ask here, as I'm afraid I may be "barn blind" (I can see conformation faults, but he'll always be my baby who can do anything in the world.. haha ) and cannot see what limitations he may have due to his conformation.

I appreciate the replies so far!

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What doesn't kill you; is sure to leave a horrible scar. 
Success is not final, failure is not fatal: it is the courage to continue that counts.