Well, without actually reading the 'dumb dumb boys short story', it's hard to say precisely. But generally, if it's about dumb boys, it could explore themes like misunderstandings. For example, their actions might be misinterpreted by others because they don't communicate or act in the 'normal' way. It could also be a comical story where their 'dumb' actions lead to funny situations.
Naruto could be one of his allies. Naruto has this knack for seeing the good in people and would probably be willing to give Obito a chance to redeem himself. Also, Sakura, with her skills as a medic - ninja, could be an ally. She might help heal Obito if he was injured during the war and see the potential in him to be a force for good.
There could be the dumb boys themselves, of course. There might also be their parents or guardians who may be frustrated, amused or concerned about their 'dumb' behavior. Maybe there are teachers if it's a school - related setting, who try to help or give up on teaching them.
There could also be interactions with the new generation of ninjas. They might view Obito as a sort of legend or a cautionary tale. Their fresh perspectives could either inspire Obito to change further or make him feel even more out of place in this new post - war ninja world.
Well, the reborn character could explore Obito's Sharingan powers in new ways. Instead of using them mainly for combat like Obito did in the original story, they could focus on using the Sharingan to understand the emotions of others. For example, they could use it to detect lies and hidden motives, which would be a unique twist on the power.
Besides Obito, Sasuke could be a main character in this fanfiction. Sasuke, with his own journey of redemption and his understanding of power and the ninja world, could have an interesting dynamic with the reincarnated Obito. Also, Sakura might play a role. She could be the one who tries to heal the reincarnated Obito, both physically if he is injured during his new adventures and emotionally from the traumas of his past life.
Often, Obito is attracted to Kushina's strength and kindness. He might try to impress her with his own abilities. Their interactions could involve Obito being a bit clumsy in his attempts at first. Kushina, on the other hand, might find his eagerness endearing and start to open up to him more. They could share stories about their pasts, their dreams, which deepens their bond.
Yes, Dabao in " Celebrating Years " was playing dumb. His true identity was the illegitimate son of the Qing Emperor and the Eldest Princess. In order to protect herself and her life, the Eldest Princess lied that Da Bao was Prime Minister Lin's son and sent him to the Lin family to be raised. Even though Da Bao looked like a fool, he was not a real fool. He was just slightly less intelligent and his thinking and reaction were relatively slow. He chose to play dumb to protect himself and his identity.
In the comics, Drax is not dumb. He may not be the most sophisticated character, but he has his own kind of wisdom and skills that help him in battles and adventures.