To build sustainable momentum toward the Luna City vision, I think we need a relatively simple and cheap first Moon mission.
A lunar cubesat (I am using the term in the small and cheap satellite
sense) to study candidate locations for outposts and settlements would be a good first mission.
This mission is doable within realistic time and budget, but ambitious enough to establish SC/SD as a player and motivate space enthusiasts to participate.
I have considerable experience in (Earth) observation sats and can help out.