I see no problem with the player passing notes back & forth with the DM, if the character's doing something the other characters ndont need to know about. If he's talking to someone in private, or helping himself to an extra share of the treasure, that's how it's done. Like the cartoon in the back of the Dragon Magazine I saw once. A halfling thief was standing there with piles of treasure around him and a innocent look on his face, while the fighter and the wizard are standin next to him in their underwear saying "Admit it Rutheford! You've been passing notes to the DM again! Haven't you?"
As for the DM needing to take the training wheels off and stand on his own two feet. I agree 100%. The only way to learn is to do. Just jump into the depool and swim.