I've seen the newest episodes of the anime, and I was thinking:
I understand that he didn't have the Rinnegan right after the battle with Hashirama, but still, I can't imagine that his recovery from that battle would be so long. He remained alive, and he was the strongest Uchiha, and one of the strongest shinobi in the world (and now with the cells of Hashirama), so why wait for someone (because Obito got to him by chance) if you can start what you want, when you want? With his Eternal Mangekyo Sharingan, he could have built an organization like the Akatsuki, and played in the shadows, just as Obito did. In this way he could have time to search for a pupil, and at the same time, the organization members would search for the Tailed Beasts, and after defeating them, keep them in a "vegetative state" until Madara awakens his Rinnegan to manipulate the Gedo Statue and collect the Bijuu's before he dies (note that he's able to steal the Gedo Statue's power, so with Tailed Beasts inside it, he could have been much stronger, despite his age).
Then pass the Rinnegan to the pupil-> Rinne Tensei-> resurrected Madara has his youth and force back, plus the Tailed Beasts are already in his possession. (And MAYBE even his pupil would've survived and both of them would possess the Rinnegan)-> straight way to Tsuki no Me plan.