SDR2 But Nao’s There, Some Thoughts:
Beginning: It’s obvious (for obvious reasons) from the get-go that Nao and Nagito are related, despite the former’s sarcastic comment otherwise when questioned on it. Nagito insists on hanging back at the beach to take care of the boy who fainted, so Nao stays with him.
In-Game: Nao doesn’t make much of an effort to be friendly with the other players, mostly choosing to keep an eye on Nagito -- who, frankly, has never been stable, and Nao knows well that he’s prone to terminal idiocy under such stressful conditions. That said, he’s likely to be put in the way of at least a few others, and there’s nothing to say he won’t make a friend to two. I feel there are some who would actually appreciate his dry wit.
Blackening: Nao has less than no desire to participate in the killing game, even to save his own skin. He’s far too proud to simply do as he’s told under threat. That may change if Nagito is directly threatened, however. If backed far enough into a corner, Nao may be persuaded to commit murder, although he has no illusions of getting away with it. He sees through the trial, however, encouraging Nagito to step up and solve the case, if only to prove to the both of them that the younger twin is capable of standing on his own two feet.
Execution: It’s likely Nao’s execution would have something to do with being dropped from a high height, or buried alive. Alternatively, it could have a superhero theme, owing to his secret love of old superhero cartoons. It would also be the most painful for Nagito to witness.
Talent: Nao is naturally reluctant about revealing his talent to the group. They are, after all, calling the entity behind their predicament the “Mastermind”, so it could get a little awkward. (Hey, look, it’s the whole reason I worded his talent thus!!) Likely, he’ll lie and say he’s some kind of Ultimate Caretaker which, due to his cold demeanor, the others are a little mystified by. (Nagito knows better, though.)
Murder: I don’t see Nao falling victim to a kill under most circumstances, he’s too naturally cautious and suspicious of everyone. The glaring exception being if he tries to interfere with a plot to kill Nagito. In that case, it’s possible they get killed together. If Nao outlives his brother, however, he will instantly become noticeably quiet, more distant than ever, not speaking a word or contributing through the whole trial. He doesn’t even try to watch the execution. It’s pretty clear his spirit is utterly broken.
Endgame: Should he make it to the endgame without Nagito, his motivation going forward would be to create the world his brother dreamed of, even though he’d never cared much for hope or despair before.
Canonically: Nao doesn’t attend class much, so it’s entirely likely that he just. Wasn’t there. When Junko started brainwashing the class. Typically - although, this can depend on the thread - I have him separated from the main plot of the game, working with the future foundation to find his brother and restore the world, and later betraying them and helping Makoto retrieve the remnants so they can be helped. (This is mostly because it doesn’t change the canon events of the game much, and makes it easier for new partners to get on board with a new character tbh.)
And Finally: A nice thought for you all. After waking up, Nagito finds Nao just sitting there. Expecting to be yelled at or admonished -- no, hoping for it. Knowing that he’s done so much wrong, and there’s no way his only family will ever look at him the same. Especially not no-nonsense, no-second-chances Nao. Who himself gets to his feet, walks over to Nagito...and there’s no scolding, no words at all, just a tight hug that seems to last forever.
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