If you guys are serious about anything, go look at ports-readmes. It does extract information from the ports tree, and creates readmes for all ports.
Currently, it's a static port. It could very well be a dynamic application. You can experiment with css, you can experiment with nginx. Preferably, don't add large dependencies (python or ruby out of the question), write it as a perl fcgi or something, you can use Plack or Catalyst or whatever. Or hey, at least tweak the templates to be nicer.
