Create automatic help and documentation.

Both are related. The help needs to flow from the relative classes and the documentation is just a pretty way of presenting the help. its a big chunck of code, so I'll sprinkle some comments to ease the review.
Yep, that is a good idea. Do you know any way of doing this from setup.py. Were we can put a string in setup.py and then reference it in other parts of the code as we build. This string is the same string that appears in README.md.