@evanstonjew The entire development process is taking place in public on the web (http://opensiddur.net for the overview, http://wiki.jewishliturgy.org for the technical details). Many of the planned implementation details are public. Those that aren’t are private only because we haven’t had the chance to write them up. If you have any questions, comments or concerns about the implementation, you are welcome to voice them on our email discussion list.

@Abe Katz I don’t believe that there is a single “true problem” in praying from a traditional siddur. In fact, not everyone has a problem praying from one or more of the traditional siddurim! For people who want a traditional text, we hope to offer access to an accurate text at a level only achievable in an online environment. For those who want to add something to the traditional text, or who want to combine contemporary works with historical liturgy, we provide the opportunity for that too. The traditional siddur itself is a compilation of works whose histories span from the biblical period to the modern period. Which works are included in contemporary published prayer books is a combination of design, historical accident, and the choices made by publishers. There is no reason to close the canon. Imparting a better understanding of traditional texts is certainly a worthy goal, and is one of the goals of our project as well. In fact, once our commentary section is ready, your essays would make a wonderful addition to the Open Siddur’s archive if you choose to release them under a free license (please, talk to us!).

Disclosure: I am the lead developer on the project.

Let me give one example of how understanding the structure of the prayerbook helps understand a prayer. Most are familiar with the Bracha of Baruch Sh’Amar. It is considered the opening Bracha of Pseukei D’Zimra, the section that includes verses of song primarily from Psalms, that precede Kriyas Shema. After studying early versions of the Siddur that were used in Israel in the Gaonic period, it appears to me that Baruch Sh’Amar is actually the ending Bracha of a section of the Siddur that the Ashkenazic community does not recognize; Tefilat Ha’Shir. That explains why on Shabbos those who follow the Sephardic Siddur recite many chapters of Psalms before reciting the Bracha of Baruch Sh’Amar while Ashkenazim do not.

Let me give one example of how understanding one word opens the door to two models of Jewish prayer. That word is “Modim.” Most translate the word “Modim” to mean: to thank. Based on that definition, many view Jewish prayer as consisting of three elements; praise of G-d, request from G-d and then thanking G-d. But the word has a second meaning; i.e. to bow. That is why Jews bow when they say the word “Modim.” It happens to be that the Kohanim bowed as they completed each part of the daily service in the Temple. We bow when we complete “Shemona Esrei” (the eighteen Benedictions). We bow because we have completed the prayer that represents the substitute for the service in the Temple. Based on the definition of the word “Modim” as bowing, some view the model of Jewish prayer as being a substitute for the Temple service. In that model it would be inappropriate to interrupt our prayers to make personal requests of G-d. Instead, personal requests are left to be made after completing our service.

Those are two of the many little secrets that lie hidden in the words and the structure of the Siddur. The answer to “Prayer Malaise” is not to fashion new prayers but to study the ones we and our forefathers have been reciting for nearly two thousand years.