Tommaso,
Thanks, great questions! Let me try to answer some of them.
The idea of the "bootstrapping mode" is to allow the survivors of a global disaster to recover from a complete breakdown of infrastructure, in which case data recovery, education, and reconstruction of infrastructure have to go hand in hand in a highly intertwined, incremental fashion. The deeper the cultural setback, the more elementary the starting point of this process will have to be. Perhaps it must even begin with reading and writing lessons. How exactly this can be done I really don't know, it is one of the many challenges of the project.
That said, let me stress that solving the bootstrapping problem is in absolutely no way a prerequisite for working on other important aspects of the repository (although I think it's one of the most fascinating problems). And yes, Wolfram Alpha is certainly worth mentioning in this context, thanks for the reminder.
Your last point of course raises many deep questions which go far beyond the very practical purposes that I outlined. At which point the repository might reach a level of complexity that gives rise to a new form of super-organism (or even consciousness), and whether we would even notice if it did, is truly intriguing. I leave this to the experts and look forward to following the debate!
Jens