Debbie -
What a laugh! Trying to teach someone to do math like me - when I sure think my way is "wrong."
But seriously, it sounds like you are one the right track. I think tht learning to enjoy a challenge is more important than almost anything else. The good news is he's younger than most, and so has an excellent chance of "getting right". My son didn't get the chance till age 10. The bad news is that to their minds, a week of "too easy work" is probably all it take to start twisting their baseline. So you will hear the shrill sounds of the mind untwisting as you apply the "supported push." And it is n't pretty. Nescessary, but not pretty. If you can give him a big picture overview once in a while, I believe it will help.
Best Wishes,
Trinity