Alright, next discussion point:
6) Desktop or Web-based?
Between the two, I say desktop. Let's face it, if the data is limited to SRD, this program is pretty much worthless. If we put it on the web, then we're limited to public domain info. If we develop it just for our own use, then we can include everything. Though I have a feeling "our" will be interpreted pretty broadly.
Another option is to develop the core as APIs, DLLs, or whatever they're called these days. Then we could have both a web based interface and a desktop interface. It also means that different parts can be written in different languages. I think I prefer this.
Web-based has the advantage that MAC, PC, Unix, Linux, whatever users can use it. But using a program that only has the SRD just isn't worth it.