I don't really think there is one true best sequence of events. For example:
1) Luna first, send stuff to space with mass drivers.
2) Gravity well is lava, mine asteroids (near Earth, then Belt) and build massive space colonies to your liking (O'Neill Cylinders, etc.).
3) Lets build balloon cities in the atmosphere of Venus!
4) Settle (likely after doing nr. 2) the ocean worlds of the kerbal-scale Solar System analog around Jupiter.
But most likely, some mix of those will likely happen, with different organizations having different needs and aims (eq. massive free flying factories and scientific instruments vs self sustained city building).
1) Luna first, send stuff to space with mass drivers.
2) Gravity well is lava, mine asteroids (near Earth, then Belt) and build massive space colonies to your liking (O'Neill Cylinders, etc.).
3) Lets build balloon cities in the atmosphere of Venus!
4) Settle (likely after doing nr. 2) the ocean worlds of the kerbal-scale Solar System analog around Jupiter.
But most likely, some mix of those will likely happen, with different organizations having different needs and aims (eq. massive free flying factories and scientific instruments vs self sustained city building).