A big concern for Caleb would be discerning what type of Jewish students made up the fraternal organization. Are they devout Jews, following both the religious and social aspects of Judaism? Were they just social observers, the ones that are rarely seen at traditional events but are always present during socials? Did they fall somewhere in between the two like he does? I believe that Caleb would be most comfortable with students that did a mix of both. People that may not attend all of the religious events but are very involved with the campus' Jewish community.
Another major concern I think he would face is deciding whether or not the members of the organization were as good as they present themselves in literature. Some organizations have a tendency to put all of their best accomplishments forward to potential member, regardless of how long ago those events occurred. There are also organizations that claim to be committed to following the Jewish principles that were founded upon. However, these same organizations are so heavily influenced by the mainstream Greek culture that many of their traditional practices eventually become non-existent. They become replaced by alcohol and sub-standard living. Caleb's personality would deter him from an organization that did not practice what they put on paper. In this case, the aggregate of the members would play a vital role in his decision to join any organization.
Sanua also mentioned the concept of "Jewish student migrancy" (p. 6). This phenomenon is defined as Jewish males' willingness to travel a long distance from home in order to attend an unrestricted school. I liken this concept to the decision of a Jewish student to join a non-Jewish organization. Once again, the aggregate would play a major part in this occurrence. on one hand, the group could offer Caleb an opportunity to interact with a diverse group of students while maintaining his ties to the Jewish community. On the other hand, it could allow Caleb to distance himself from the Jewish community and explore the university outside of its watchful eye. The latter could have positive and negative consequences. My only knowledge of this type of interaction is when a Jewish friend of mine told me how the members of the fraternity he was trying to join drew a swastika on his back. That experience was enough to deter him from joining the Greek community in any capacity. I could not see Caleb joining any organization that would put his faith or his personal beliefs into question or criticism by those who do not understand them.
Resource:
Sanua, M.R. (1999). Jewish college fraternities in the united states, 1895-1968: An overview. Journal of Ethnic American History, Winter 2000, 2-42.