I'm not good at critiqueing. I can give you the basics but so can everyone else. And they can also give you alot more information.
But I want to say that his persinality sounds alot like my guy. My boy learns really quickly and is constently testing me and trying to outsmart me.but he's a saint of a horse, and he's more then patient with me. But by doing that and testing me, he has taught me ALOT. And has made me a much better horse person, and i'm still learning and always will be. Take everything he gives you, and learn from it. You'll make mistakes, he'll confuse you, and you'll confuse him but that's part of horse training. Don't let it get you down. Take what you can from the experiences and move foward.
I know you mentiond sending him to a trainer. If you can afford it I HIGHLY recomend taking lessons with him. For ground work and riding. I can honestly say that I don't know what I would have done if my instructor hadnt agree'd to come give me lessons on my boy.
Anyways, that's all. Sorry I didnt do any conformation crituqeing but I just saw your last post and I felt like I needed to comment on it. As I feel for you. I just bought my boy 5 months ago. Before that I had done 13 years of lessons. But lessons are ALOT diffrent as I found out. Owning and riding outside of the lessons is a whole diffrent animal. I can't thank my instructor enough for helping me though and helping me progress even more