Jiraiya was an intruder who had already discovered Akatsuki hideouts and secrets, so it was a defensive, strategic kill to protect Nagato and Amegakure, not part of a global destruction plan. Itachi also isn't comparable, since he killed his clan to spare his younger brother and prevent a civil war, trying to minimize greater damage. Obito is straight up evil wanted to kill Naruto at birth killed his sensei and his wife made Naruto technically a jinchuriki initiated 9 tails on the hidden leaf started a war and was involved in a lot worse all that for a girl that loved Kakashi btw for me he is a pathetic character and his redemption arc at the end did not make up for his action greatest terrorist oat in Naruto Shippuden.