BECAUSE I LIKE TO TROLL YOU.

AND YES. In real life too, he can relate to these characters so well because he's been there and done that. He tried so hard trying to impress people and made them happy. And he finally did it. By playing these characters, it's like him wanted to support them to not giving up and try harder even after they died. Kondo never gave up, trying to reach out to Naomi with his song. T_T