He didnt win anything, people need to eat. People in an infinite Genjutsu cannot eat. Naruto is able to break out of it considering his consciousness can literally be in the tail beast plane at anytime. This plan was well prepared and well set up but the goal is retarded. Think about it. Only thing that needed to happen for the whole plan to go down the drain was obito getting killed. Madara didnt know what ability Obito would unlock with his sharingan, for all he knew Obito would only be able to transform into the shape of a duck with his MS tech. On top of that What if when pain died konan destroyed the eyes? or the eyes decomposed like they were suppose to. Or what if Konan would have made her explosion like 15 minutes or what if Kabuto decided to take full control of Madrara, or if it were itachi or sasuke vs pain and not naruto and they used the black flame to kill nagato, or obito developed the same disease as itachi, or if the jinchurikiis were 2x as strong as they were when they fought th akatsuki, or if itachi used the body flicker guys jutsu on obito and made obito promise to protect the leaf forever, i mean the possiblities for a major f up are huge.
Credit is due becuase he had to stall naruto and sasuke from killing him to get the plan done, he couldnt even beat em he had to stall em with rocks and clones.
