3 rounds of torture

Round 1: Can Ibiki crack Itachi to get intel and if so how long would it take/difficulty.

Round 2: Can Itachi make Ibiki break and give up intel if so how long does it take/difficulty.

Round 3: you are captured and told you get to choose your torturer, who will you pick? (Less scared of/think you could hold out the longest against)

Rules: no killing, and no escaping being captured.