Hi GGG, Just off the top of my head, I think #2 of what you MUST have isn't something that H will either want to do or think he needs. It also could be seen by him as saying HE is "sick" or "wrong" and not your business. It seems like more than a "boundary" and would be seen by an MLCer as you trying to "fix" him.
Don't get me wrong, I think it's a really good idea for him to go and he should. I just don't think he will take it well.