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This challenge seems incredibly intriguing and well put-together, and I certainty admire how a million dollars have been used to improve DnD specific AI!

I believe a small team (3-4) of dedicated writers, co-ordinating each other online, has a genuine shot at writing a quality Story Arc quickly and bagging $20,000, to be spilt proportional to work. I have ideas about how to quickly streamline the process of multiple people working on one single Annotated Dungeon Run, and think we can really expedite this process in a number of significant ways. If interested, please contact me through my account on LessWrong- we can swap drafts, talking about writing commitments and get a good feel for fit before committing to anything.

Also, to those with the enterprise to attempt to scale the project up, I believe I can find around 10-20 people, (given enough notice), with considerable storytelling ability willing to write annotated dungeon runs as a part-time occupation. I have unique access to exclusive TTRPG internet communities and artsy university students looking for casual work over summer- and I would be happy to find and direct them to you. If you want to work a deal out, also message me on LessWrong. 

I have some ideas about how to scale up and extradite this project, and am happy to help bounce ideas around.