We haven't figured out even half the answers for #1, but we're in a bit of a pause. Familiar patterns, familiar problems, familiar management.
On the other hand, #2 is raising new questions. He's fairly "classic" Asperger's (which is a bit like saying someone is a "jock", meaning there's a lot of latitude in there), and has a typically low tolerance for challenges.
Some people seek out the hard stuff, because they enjoy the struggle for mastery. The easy stuff isn't interesting.
He's not like that.
If something's not fairly easy, he doesn't like it. Struggle is not his thing. Perseverance is illogical.
That's not a recipe for living well in a world that's usually outside his comfort zone.
So how do we teach "frustration management" and strengthen his limited ability to persevere?
Some quick web searches turn up "kid stuff" -- techniques that work for neurotypicals but that we've long ago exhausted. We've got the techniques, what we need is a multi-step program. We need to figure our a staged sequence of progressively more challenging tasks, balancing those with things he likes, while training on techniques to manage the emotional content of frustration -- understanding how to work through his initial responses ...