Princess Celestia:
As you might noticed, Princess Celestia is a character that fascinates me for two reasons, the first one will be her background story and her position, and the second one will be her personality, something that I found really Interesting.
There are several factors that should be consider from Celestia, the first one will be he status among the other existing ponies that lives under her rule, the second one will be her background story and past events, and the third one would be her age and experience, Celestia lived by 1000 years, probably even more, this makes her very aware of the different events and multiple outcomes of these events, but such knowledge will make her feel tiredness of experiencing the same situations multiple times, this will converge in a status of constant boredom.
Boredom is a critical consideration in Celestia's personality, after all, this status is what impulses her to make actions that qualify her as Troll, but is not the trolling what she does, is more like planned situations, unlike other ponies, she wants to stay away from the spotlight, and she wants to see how events develop given certain circumstances, which is diverted in some sort of entertainment, everyone's entertainment apparently, she can be consider as the architect, the planner or just simply the designer of the situation, which is created for her entertainment, this is shown in episodes like The Ticket Master, A bird on the Hoof(Philomena acts as a reflection of Celestia's personality), and of course The Grand Galloping Gala.
And then, there is also the Luna incident, which portraits two aspects of her, the first one would be an assurance of the skill she has, and the second will be the outcome of the decisions she makes, her decision of banishing her sister to the moon is open to interpretation, there is no record of dead in MLP universe and there is also no record of Nightmare moon's motivations that caused her to be banish, if such events were clearer, then more aspects of Celestia will came out to the spotlight.
There is another aspect that should be address, the actions that she will probably take after seeing one of her plans fail, the reactions to such situation is unknown, but knowing this reaction will provide a clearer view of the real Celestia.
I always wondered how the fact of always being correct creates an status of non-existing corrections, that will be something that should be worth of seeing, since this kind of personality is rarely corrected, due to the pre assumptions created by the image, is really fascinating to see how one of these individuals will be corrected in an environment of equals.
That will be an answer that I'll be looking forward to see in the upcoming time.