Perhaps the archive of 419eater.com could also be used to train algorithms to write plausible emails. They already have a lot of email responses to scammers on file.
Good Idea for the next round of YC founding? I mean, five nines of that is above my head but sounds doable. How HARD is that to actually be implemented?
If you can't, there are still benefits to be had. Have other loosely-related, monetizable projects. Execute the plan with an intent of garnering massive media coverage. Build your personal brand and reputation. Leverage the fame to jumpstart the marketing on the other projects.
I was hesitant to click that link due to the name of the directory, but then I just realized my eyes were experiencing keming... http://www.ironicsans.com/2008/02/idea_a_new_typography_term...