"An initial poor showing will make improvement on successive runs more profitable." Qui-Gon would be having a field day. Obi-Wan simply takes the pragmatic look. They aren't making anyone gamble for or against them, merely presenting a certain level of competency (or lack thereof) in order to provide for themselves. However they move forward in this place?

He's less certain of signing on with the military if he's to keep Anakin trained and safe. Providing for them is one thing, but the expectation of conflict? Of war?

Anakin's too young. He's too young back home, and as little as he cares for it- they had no choice in the matter. Here? They do. If his arm tightens somewhat, protective, around Anakin's shoulders?

There is no one here to reprimand him.