mw,
I think one of the issues that's related to is active vs. passive messianism i.e. can we help bring that time to pass or will it happen independent of us? Despite my lack of belief in a messiah figure or even a messianic age I tend to favor an active approach that doesn't get into particulars. The danger in active messianism is when one does get into many particulars.
One drash I've read on the concept of messiah relates it to oil as a lubricant. In that sense the more we can lubricate things, reduce friction, the more we are all making a messianic time reality. There's a book I'm going to be getting probably in my next amazon shipment that's by Raphael Patai.
Amazon.com: Messiah Texts: Books: Raphael Patai
It's really just an extensive compilation of translations of Jewish sources on the messiah. This is from Reb Yonassan Gershom's review:
"Patai does not seek to present any particular doctrine as "the truth," nor does he seek to convert anybody to anything. He simply presents all the materials he could find, with some academic overviews of the basic themes. His approach is that of an academic folklorist, not a theologian -- in fact, the book is subtitled "Jewish Legends of Three Thousand Years."
The chapters cover such things as pre-existent names of the Messiah, prophecies, apocalyptic writings, birth of the Messiah, stages of the Great Redemption, Last Judgement, Resurrection, dreams and visions of the future world, etc. There are sources from the Bible, Talmud, Midrash, medieval texts, Hasidic teachings, and modern accounts. Plus there are literary references to the Messiah from such writers as Elie Wiesel, Scholom Asch, Martin Buber, Jacob Wasserman, etc. All in all, 337 pages of prime material."
The different beliefs, particularly the non-rational ones interest me much more than the watered down stuff devoid of much myth that's so frequently passed along today. One of the things I'm especially looking forward to reading about is some of the parallels in the Jewish concept of the messiah to other religions that may have over time been de-emphasized.