Highmoon,
Now you know 3. (Working our way towards a minyan.)
I am a Reform Jew, so I do have less restrictions. However, I view Shabbat as a day of rest and peace. For example, while I do game and write, I try to do so in ways that do not constitute work for me. Fortunately, my group games on Saturday evenings. (I am usually at temple on Friday evenings.)
My advice is to follow the dictates of your faith and your conscience. If you need to, ask for advice.
I have seen at least one gamer with a kippah at Gen Con. So you should not feel uncomfortable. Most people at Gen Con are quite nice. (You could also attend a few good seminars during Shabbat.)
You might want to check out the information on Indianapolis at
http://www.thedociverse.com. I seem to recall that there is a kosher deli fairly near the convention center. I hope to make the convention this year.
Rav, the Tanakh (Hebrew acronym for Bible, from Torah (the first five books), Nevi'im (Prophets) and Ketuvim (Writings)) or Bible (Old Testament to Christians) is the holy book of Judaism. The Talmud (sometimes called Gemara) consists of sixty-three books of legal, ethical, spiritual, theological, ritual, and historical insight. It is the primary record of rabinic discussion from the fifth to seventh centure of the Current Era. (Abbreviated C.E.) It is a major source of study for Orthodox and Conservative Rabbis, and Orthodox Jewish religious law is largely based on decisions in the Talmud. The Midrash, composed at approximately the same time, has several commentaries on the Bible.
(Most faiths do have their own body of literature. Touching on gaming briefly, I imagine that in most fantasy worlds each faith would have their own attendant body of literature.)
I would love a d20 kippah. (I have seen Chicago Bulls kippahs, by the way.)
Shalom aleichem (Loosely translated "Peace unto you.")