Challenge is what worked for DD10. When she was 8 she was in a grade 4/5 French Immersion split in which many kids were 2 years older (and most a head taller... poor kid! lol). Anyway. It saved her... it really did. She needed to get her butt kicked. Sure enough, this year she has much better focus, better study skills, organizes her homework time independently, and isn't plagued by perfectionism.
DS8, meanwhile, is the same... he needs to be CHALLENGED or he's on the moon somewhere.
When you say: "Here's the problem - he genuinely doesn't know HOW to try. He's never had to. So for him, if he doesn't completely get it within a few minutes, it's a lost cause." ...this was my DD. She would learn at the speed of light until she crashed into the wall of "just a little too hard" ...and then she'd be DONE. I had to toss her in the deep end (too challenging to be perfect) to get her past it, but it worked.
