Rereading the school days arc in vigilantes for what has to be the twentieth time and something I really enjoy about Oboro is kind of like... how casually encouraging he is?? You can see it especially with how he interacts with Aizawa, but he's very good at just providing support and believing in Aizawa, who's lacking in confidence, as a person - but like in a very relaxed sort of way.
He just doesn't make a big deal of it! When Aizawa's talking about his quirk and the reasons he's insecure about it, Oboro immediately responds by suggesting that he use it to trip up villains, and talks about the ways his quirk is actually a real talent. He's being encouraging, but he doesn't act like... overly concerned, or upset with Aizawa for the negative self-talk, in a way I feel like could unintentionally come across as patronizing?? I don't know how to describe what exactly I mean, but... I guess the way I'm thinking of it is that he doesn't dismiss Aizawa's concerns out of hand as irrational, but gives him practical advice, in a way that's also affirming his capabilities at the same time.
And when Aizawa's struggling with having messed up against the villain in their hero study work, he helps him figure out how to deal with it next time without making it a big deal. He tells Aizawa in their conversation just before his death that he could do anything if he puts his mind to it, again encouraging him, but in a way where it's clear that he genuinely believes it - it's just something that's obvious to him.
It just gives me the impression that Oboro was aware of Aizawa's issues with confidence/self-esteem and on some level was looking out for him during their friendship, but he obviously sees him as an equal too! And even looks up to him, I think. It's not something stemming from pity but just second nature to him... he doesn't push or make Aizawa uncomfortable trying to help, but he's still not letting Aizawa think badly of himself if he can help it either.
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