Hmm. It looks better balanced without any pad. The front tree angle is a tad steep for his shoulder, but not bad, and the width is decent. I don't think it needs to be lifted up at all. However, the Ultra ThinLine Trifecta pad will give you some protection, and you can get some rear shims and play around with it. See how it rides with and without them.
Whatever you do, do NOT use that wool/sheepskin half pad again, and make sure your reqular pads are THIN.
How does his sweat marks look after your ride?