How do Daniel's view of Rosh and the attack against the caravan seem to contradict one another? Why did Rosh attack the caravan, and what is really going on?

Daniel looks up to Rosh, seeing him as brave zealot whose example he wishes to emulate. Over time, however, he comes to be disillusioned with Rosh and his methods. Although Rosh purports to be a liberator of the Jewish people, it's often Jews who end up being robbed and beaten during the regular raids that he leads. And that's what happens in the raid on the caravan.
Daniel's initially warm feelings for Rosh aren't reciprocated. Rosh never takes Daniel seriously, and he doesn't hold him in particularly high regard, even after Daniel proves his bravery. The raid on the caravan provides us with an illustration of just how little regard Rosh has for Daniel and his abilities. Daniel wants to prove his bravery, but Rosh orders him to guard a large, scared man while the others get to do all the daring stuff. Daniel would much rather have been involved in grabbing the large slave, which was the whole purpose of the caravan raid. But because Rosh thinks of him as little more than a kid, Daniel doesn't get this opportunity, which makes him disappointed and frustrated.