I think if we re-thought out the game of Civilization, but for colonizing the moon and mars, we may see that there is a way to have 5-10 humans controlling 10's of thousands of robots. It seems like the first step is to seal off a bunch of caves, or build bricks for buildings, or both. Perhaps creating a machine that could round up and process materials for a huge 3D printing machine for enclosures. Run that to build spaces. Collecting huge stores of water ice may be a step, and have them next to processors for water, oxygen, and rocket fuel. Nitrogen seems to be a problem to be worked out. A step may be to bring seeds, and start growing them in pressurized, radiation free spaces, then bring animal embryo's and "grow" animals. After there are 5,000 or so of square KM of pressurized space with plants and animals, then consider taking more humans in. 1 machine like the boring machine may be enough both create new habitats, and bring up raw materials. I suspect that the lower gravity MAY make it easier to dig. When they develop the technology, and find the raw materials they find to both create plant growing lights, and an energy source, then Bingo, self sufficiency.