Madara the fortune Teller or Mastermind of psychological warfar
Well there was pretty much discussion about that madara planed this whole thing about Rin & Kakashi.
But there are some Questions left, and i may have some guesses.
Q: First, How did he knew who Kakashi & Rin were, and how they looked like?
1. PA: Zetsu made researches for Madara, after Obito talked about them in their dreams. After He refused to help him because of Rin & Kakashi, Madara thought about killing manipulating Rin the one Obito is closest, and to make her like Yagura(maybe possessed by some Mindcontrol?). So Madara found out Kakashi has Obitos left Sharingan, maybe he wanted Obito to get his Eye back to achieve his full power.
2. PA: Madara maybe has the ability of fortune telling, or he got it told by someone wiser like the old forseeing frog. So Obito maybe was the chosen one for Madara to fulfie his plan, i mean it is kind of impossible for him without Zetsu help to get information about anything outside the world. Madara cant leave his cave, so he had to stay there for years, and controlling bloody mist seems hard this way, witouht beeing able to use some Techniques. ( Zetsu may be a possibilty, but we do not know how, and the guess of an mind control jutsu by zetsu seems not really plausible, maybe they just killed him, and a clone did this work, so this is why sanbi also hadnt a host?)
(The next Question is a really intersting one and its fully made up by an old theory involving Shisui.)
Q: How does the Mist Ninja(with the Byakugan forgot his name) know Shisui? and what has Shisui to do with this whole storyline?
PA: They faught vs echother, this was what he told us. But why? Well the time of Bloodymist could be the answer, after this Happing because of Kakashi, he joined the Anbu forces. Where Shisui maybe also was part in. We all think Shisui is as old as Itachi but i think he is as old as kakashi. Because this whole Bloody mist thing started early when Kakashi was around 9 years old. And i do not really belive that a so brillaint and called strongest Uchiha as Shisui would be as old as Itachi(13 when he died). Well what is his position? I think he might be Obitos brother. Madara maybe also found out about that, so this is why Obito was needed to get the Mangekyo Sharingan. We saw that Shisui had his MS, but how did he get it? Obivsually someone told him how to do it, and most likly it would be Obito or Madara himself, as done with Itachi. Shisui was the key for Obitos own EMS and Maybe Rinnegan, what is a reason why Obito did not took Nagatos Eye earlier. Shisui is to important to be just a fodder, and his appearence resembles kinda Obito, as well as his nickname Shunin no Shisui. We all thought him to be Tobi some time, after we found out that Danzou hat his Sharingan. So the Mist Ninja was part of the Bloody mist, a time where Madara controlled this village, and a reason for Shisui to fight vs them lead by a special mission. So Shisui before his death maybe, was the one who told Itachi about Madara/Obito and so itachi went to search for him. Its maybe a good reason to assume he is Obitos sibling, because we see Obito not wanting to give Kabuto the DNA of Shisui and he covers the dmg eye, even it is not usable as if he maybe serches for a way to retrieve it back.
Q: How did Obito slipped through a Rock without having his MS?
PA1: Maybe by the Blink of an death his own life force fading made it.( dont really think so but everthings possbile as Kishi wants)
PA2: Body transfering is usealbe without MS( Seems most like a good possibity, cause we often saw Tobi using this Jutsu witouht MS activated, maybe he is special?)
PA3: Madara somehow knews every Sharingan ability, that an eye has so thats how he knew wich eyes had the power to achive Sasunno etc, thats how Obito got to know this information about eyes. So he just lied, and let Zetsu bring him down there to threat him.
Q: Did Madara chose Obito or was it just random?
PA1: He chose him, by knowing he would be there at the right moment, to threat him at the right time. Seems a bit to farfetched to thing this many lucky events happend for obito an uchiha to appear at the right moment, at madaras cave lol
PA2: It really was Random Luck, and Madara now knew he had an Uchiha on his side.
Q: Does Obito maybe know, that Madara was behind Rins death or was Madara not even involved?
PA1: If MAdara was not involved then he is an fortune Teller for sure!
PA2: I guess Obito really found it out later, but it did not matter anymore because the plan of madara seemd to be the only possible way to have the life and the world obito wanted to live in(with Rin maybe). Its also possible that this is the reason why Obito did not revive Madara, and was afraid of him to found out about it.(Nagato could maybe be hold for to revive Rin? Maybe Madara had her Body hidden somewhere? ) Thats why he did not blame Kakashi, because he knew it was not his fault, more over the fault of wars. I mean afterwards he killed tons of Ninja without realising it, covered in blood, telling us he is in Hell. Its seem like he had a trauma, and left this place maybe with rins Body to ask Madara if he could save her, and so Madara tells him that in his inifnty tsukyomi world he can get her back to live, if he helps him to achieve this.
(Q = Question)
(PA = Possible Answer)