YES!!!!!I was thinking about the Uchiha massacre... It seems to me that Itachi found out something very very dangerous and terrible so he began a long long plan for that.
What he discovered: the existence of Tobi, which was of incredible strength/ability. Itachi knew at that time that he hadn't the slighest chance neither anyone of the Uchiha to defeat him.
His plan: Since he can't defeat Tobi, he thought to make/educate/prepare the one that will be able to defeat Tobi... and that is Sasuke. Ie: the reason Itachi let sasuke live was so he will get stronger, then he will awaken the MS, then fight Itachi, then take Itachi's eyes.. so what I say is that Itachi planned for Sasuke to take his eyes at the very moment of the Uchiha massacre... so Sasuke defeats Tobi one day.
This reminds me a little to what Minato did when he sealed the Kyubi inside of his son Naruto.. he knew he couldn't win.. he planned and saw that one day Naruto will be strong, control the Kyubi and defeat that one behind the attack. This shows that Itachi/Minato faced the same guy and without even planning this together saw that Sasuke/Naruto will defeat him some day.
About the details of the Uchiha massacre.. The elders, Danzo, the Uchiha's real mentality, etc... I'm sure Kishi has a lot of things to reveal to us.. still..