Setting Down Broad Brush Strokes for Next Project

I've been asked to re-write my coding nemesis. It needs to do a lot more in the next cut, and there's just no way the existing version is going to be able to "stretch" to fit these needs. What I needed to do was to get the broad brush strokes down... the main ideas... on paper so that I was sure things would fit together and I'd be able to get the project working in a reasonable timeframe.

That's why I was looking at the embeddable web servers, among other things.

There's a lot to do, and dividing up the work between myself and the other guy working on the project needs to be worked out as well. Again, just the big broad strokes.