Hi Thomas, thanks for sharing this idea.
Something like ask.orgmode.org with a StackOverflow interface would be very nice. I am copying Jason, http://orgmode.org webmaster, to make sure this would not add too much work for him. I am not afraid of fragmentation of information: as long as this new interface links to relevant primary sources of information (the manual, Worg, the mailing list), these source will be used. I'm more afraid of fragmentation of the _energy_ that people put in maintaining those primary sources. But at the end, I guess things will auto-regulate and the overall UI for finding information will improve. At least there is nothing wrong in trying. What is the next step? -- Bastien