Your thread was a really nice read but I don't think Kishi would have thought this for the Plot of Naruto and Charector of Obito..
But you both have excellent obsevation skills especially the comparision of mask really impressed me...
Everyone has its own thinking so am I.Sorry but I disagree from most of your points above....
You are trying to present Obito in a very positive manner.I think you are comparing him from Lelouch of Code Geass.Now let me clarify my own views in contrast of yours
1)Differences between Madara and Obito-
Obito was deeply influenced from the thinking of Madara.He carried out the Dream of Madara like it was his.But like Naruto he has a big ego.He doesn't want to think himself as a mere pawn of Madara.As from the starting he doesn't expect Madara to be bossy on him.He wants to show Madara that he is the one who is doing favour on him and Madara has no effect on his thinking and decisions.Although deep inside he has accepted Madara's leadership and that's why he reincarnated Madara,other wise he already knows the attitude of Madara and also has the Rinnegan.He could had also contolled Juubi.But he wanted the plan to come in existence,he wants other ppl to be happy and for that he is even willing to give away his own life for Madara who has Tsukyomi as his Mang Sha ability.
Secondly on the same manga page he didn't neglected Madara's will.He just postponed it for the time he proves to the Shinobi Alliance morally ,what he is doing is correct.He wants to influence them.and for this he is using the power of despair and loss.for eg the impact he made on Naruto after killing Neji.He wants the shinobi's to feel what he feels.The truth and advantage of Tsukuyomi upon reality.
2)Kyubi Attack- The Kyubi attack was one of the first things that Kishi added to the series.At that time I don't think Kishi must have even thought once about creating the charector of Obito.When the storyline of Naruto came at that position where he had to justify the old events of the series ,he had two ways for retelling the Kyubi attack.
First Kyubi broke free itself and second that ,the incident was planned by someone.
If he had taken the first way then it would have been too much simple and obvious.
After adding Obito to that incident Kishi hit multiple targets with just one arrow.
Firstly he justified the Charector and role of Minato Namikaze as the Fourth Hokage.Through this he was able to provide a Heroic death of both the parents of the protagonist of the series.
Secondly he actually inacted the impact of Mang. Sharingan on Nine Tails.
thirdly he more intensified the Villanous role of Obito.
Fourthly he filled the timehole of Obito's presence after the Kannabi Bridge Incident.Fifthy he clarified that the Kamui is not invincible,Sixthly he reshaped the history and made it what it is today...
you can say that Obito's decision of attack on Konoha was a Victam of the Plot settings.
After obtioning a MS with ability like this and Senju cell he started cosidering himself invincible.After being thrashed by the fourth he must have ralized that he underestimated the legends of Konoha.After this he would have also realized that he has to value his life untill the collection of all the tailed beasts so he decided to be away from Konoha and transffered thesr tasks to fellow members of Akatsuki....
After the fourth's death Naruto was in protection of the third and he did not wanted to face or underestimate him now. Hence leaving him alone for the time, Obito's grews himself up also from 14 or 15 year old teen...