thank you I pick Shikaku for at least trying whenever he can. Tobirama and Orochimaru too.
Hiruzen lost major points because of Orochimaru. He noticed Oro was twisted and disturbed as a child. He was willing to die for Konoha instead of Tobirama and Danzo before he was granted title of Hokage , but instead of arresting Orochimaru he decided to let him go when he noticed he was responsible for killing Leaf citizens. I guess he would have had to kill Orochimaru as opposed to just arresting him ,but still. He's too emotional.
This is hard. I don't know. I would say Kabuto. But, that's my opinion. He's shown his extremely capable. With enough time, I'm pretty he could of done more.
they are smart in different ways. orochimaru is the genius, kabuto can't be greater than oro because he was only finishing what oro didn't finish. when it comes to strategies, it's shikaku, of course. shikamaru still has to prove himself equal or greater than his dad.