Okay, so the game's difficulty is based mastery of player skill (rather than skill points)? I like that!
I'm guessing we'll do a workflow to generate some content and then review if it fits what we want, right?
And if you're going to onboard talent from a number of sources; how might you handle conflicts where nobody is in the wrong, but it's difficult to make the product come together? Are you thinking scrum-based task-to-task missions for the team or perhaps this entire project is but a dress rehersal for a future project down the road (ie. finding the bits that work, noting why they work or dont work, and restructuring it all together so that it will be a smoother process for the 'real' project)?
Jumping off that last point... what's the smallest project that can be done, that will be most useful for any future project?
* Perhaps we'll need to make some character information and interaction system? (And if so, what form would it take? It feels like a content contributation framework like conceptnet.io or feather.wiki would be helpful for onboarding writers into the project. But the main issue would be how the game could update itself from the living document.)
* Perhaps there may be need of a test bed for staged testing to ensure functionality with every update (and each supported computer type)? Even if you're not using custom plugins or preset library modules; as core design team, you're going to have to made the decision on the approach with respect to the mechanics. (ie. isometric vs top-down vs sidescrolling vs FirstPerson & hexagon-grid vs square-grid vs pentagonal-square-grid vs MultiUserDungeon/InteractiveFiction 'rooms'.