This is something I'd do with shell scripts called from a makefile, while converting markdown to HTML using pandoc. Of course, the shell scripts would have to use find, sed, grep, and cut to generate the indexes.
i know a little about shell scripts thanks to the insane linux customization community, but not nearly enough to do something like that. grep has always been kind of went over my head even though a lot of linux users seem to swear by it. would you happen to have any resources for learning more about shell scripts?