I judge based on time duration and the student themselve. This is also why i dont take my time with folks on NB. They are quick to call somebody a hater when they know the truth hurts, all ive said about jiraiya is true, he is by far the worst teacher and the fact that you have no decent reply other than, im a hater shows that you know this. Seriously, this is what im supposed to argue against

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Out of the sannins work on their student's orochimaru takes first place. We saw how sasuke held his own against team yamato to leave naruto gob smacked and acknowledge that he needs to improve.
Tsunade takes second place. We saw sakura's medic ninjutsu prowess when she healed kankuro and developed an antidote for sasori's poison. She showed great chakra ability to release it to improve the strength of her punch/kicks.
Naruto's development under Jiraiya pales in comparison with these two