ADHD Teens Online Support Group

My son has had ADD for quite some time now and he only very recently (two years?) has been on medication because we tried everything under the sun to try and moderate his behavior without medication.

He is in seventh grade now and is easily smart enough to do well in school but has serious problems with discipline, motivation and organization. I know that even without ADD he would still have these problems because he is a teenage boy and that is what they do.

The problem I am having is that he goes throughout the quarters in school with usually B's, C's, D's and F's and then usually manages to pull out C's just at the very end of the quarter and then only because my wife and I start talking to his teachers almost daily, watching the grades as they pop up in his classes or lack thereof.

We have considered holding him back and in the same breath moving him to another school so he doesn't get stuck with the stigma of being the kid who was held back and whatnot.

What I'm really looking for here is some input on "How much help is too much?" Some of his teachers have suggested that we let him fail and get held back while others think that would be the worst thing we could do.

I am starting to feel that holding him back is a logical action at this point because he would not be able to pass if I wasn't watching over his shoulder. If he was able to pull out C's at least without help then there wouldn't be a question as to letting him continue. I just feel that school is going to continue to get harder and I would prefer to hold him back where he is now instead of waiting for him to actually end a quarter with all D's and F's because then it isn't our choice.

Thoughts?