I think any Cosmostrategy should leave room for Space Colonies to be independent of Countries, Earth based NGO’s or Multinational Organizations. They should not be Colonies at all but independent sovereign entities.
I think the earliest possible independent space sovereign would be a sort of Space Station, preferably not in Earth Orbit. It should be conceived to be mostly if not entirely self-sufficient using Lunar or Asteroidal resources. The station citizens would become space/zero G acclimatized and in compatible with living in High Gee. While not a new species they might evolve many differences. It would be interesting to see what kind of social structures these Stations (if it works they would probably proliferate) would develop.
I don’t know how many generations it would take for these Stations to payback their loans but I suspect that they would eventually turn a profit or at least the ones that survived.
Me I would like to see someone push a version of the ISS into lunar orbit and pair it with a robotic mining system on the moon to provide lunar resources to be processed on the station to support the station.
The Lunar Mining system would need to be developed and functioning first and that would be my focus today if I was leading NASA or SpaceX or Blue Origin. Put a large solar power station on the Moon to power the Mine and Catapult or Space Elevator to move product to Lunar Orbit. Of course robots would install the solar panels and assemble the catapult and then do the mining.
On the Lunar ISS when it finally gets there with its permanent residents and children and sperm/ova bank. It would need equipment to refine and process the lunar materials into something to sustain and expand the station or be traded for new modules and other things it can’t make for itself.
Forget sending people to the Moon or Mars any time in the next few decades and focus on sending robots to build a sustainable infrastructure.