(1) Assuming Starship makes it to orbit, it enables a range of structures larger than the ISS but smaller than the O'Neill colonies. A mission to Luna or Mars involves 12-20 launches of fuel tankers, for the same cost you can put up a
lot of mass to LEO. A really flashy space hotel seems practical, as would simulation environments for Lunar, Mars and Asteroidal technology development.
(2) O'Neill colonies with large airspaces seem impractical because you'd need large amounts of nitrogen or some other inert gas: you can find oxide rocks everywhere in space but pure oxygen environments aren't safe. On the other hand, the atmosphere for an LEO baby Bernal sphere would be about 15 Starship loads and probably worth it for the visual appeal.
(3) The later work of O'Neill's students focused a lot on manufacturing. The proposal to build large structures by vapor deposition of metals onto a balloon still looks feasible. The solar power satellites shrank considerably in mass and it seemed that they could be built more practically from terrestrial materials.
(4) Any space colonization effort runs into the problem that it needs to be self-sufficient in terms of manufacturing (especially Mars) which led Eric Drexler to go off and develop his vision of molecular assemblers. Drexler's proposals haven't aged well but something equivalent that combines 3-d printing with flow chemistry, synthetic biology, fermentation and other technologies is probably possible -- and I think is the critical path. That flashy space hotel, however, really is about rocketry and space assembly of large structures which really is the unique application of space manufacturing; I don't think space manufacturing can ever be competitive for the terrestrial market but it can be competitive for things that can only be made in space.
(5) Colonization of Ceres dominates all other space colonization opportunities in the solar system because there is no shortage of water and no shortage of nitrogen. It seems possible to take the whole thing apart and build a colony with more floor space and a larger population than Earth. You don't get the 0.2 cubic kilometers of ocean that we get, but I think you can culture all the fish you can eat anyway.