First of all, Itachi was a hero because the Uchiha clan wanted to take over Komo, but he stopped it, even tho he had to kill everyone. He knew what was war like and he feared it, so he did what he had to do in order to achieve peace. He took on an unimaginable weight on his shoulders, like no man would ever do. If he would of refused, either way his family would of been killed in the war, and what good would that make?
Failure as a brother? What manga have you been reading? Itachi wanted him to become strong, and to protect him, not having leaving him experience war like he did himself. Your not even making sense, do you live in the 3rd World or something? Itachi never attempted to kill Madara, he wanted to fulfill Sasuke's revenge, and have Sasuke go back to the village. Worst nightmare? what are you talking about? And what do you mean by the strongest uchiha? He's a mestermind but he's not the strongest. The strongest eye technique lays in Shisui's eye, imo. Get your thoughts right, and come back, because this hurts my eyes reading it.