Cloaking pre-requisite is Hiding Level 2.
you can check skill simulator.
how long would you plan to use the skill hide? like 5 mins afk? (then max hiding) and it will reduce the sp consumption and longer time.
He will ask you a few questions but you can answer them in any way you want. Then if you are at job level 50, you get to choose one item between a Jur, a Katar, a Main Gauche, or a Gladius. Otherwise, you will get a Jur, a Stiletto, or a Katar (randomly determined).