...continued.
Even though HLS could land earlier than 2028, it seems the HLS program is approximated for 2027 at the earliest. Then, in one year Starship may fly many experiments, so 2029 doesn't seem impossible, with some margins, to start flying Starships with crews from the Earth to LEO - and back.
Then an interesting thing happens. HLS is planned for at most 4 people - but Starship can bring many more, up to - especially in short flights - a 100 people. This is aviation level numbers, effectively passenger flights. Can we estimate when those flights may start happening?
Nobody flew to space more than 8 people in a single vehicle. Maybe it will take extra time, care, engineering efforts and red tape cutting to make sure that 20 people can fly in Starship, or 60 people, or 100. So far we see tremendous progress in Starship program over the last 5 years - but so far we saw mostly building, and the next 5 years it will have to be much more of flying. How many "crewed" flights Starship will need to complete to start flying e.g. without secondary safety system, possible only for small crews? To start flying in "passenger" mode?
Maybe it will take 3 years. Maybe 5. Or more. Maybe we shouldn't count years but how many times Starship flew and landed. We should take into account the speed of licensing organizations - because allowing to fly with passengers the system of the kind of Starship is not a small feat at all. At this point we're well in the guessing land. For example, it might be affected by the attempts of the Starship to fly to Mars - and especially to land there. Maybe SpaceX will have to amend the Starship to add some extra protection for landing. However, a lot could happen in 5 years of flights, if Starship will be flying with the frequency anywhere near it's planned for.
So maybe by 2035 - or even earlier, but also possibly later - we'll start seeing Starships bringing to LEO tens of people in a single flight, and then bringing them back to the Earth. It's interesting how the manned spaceflight in general will look like at that time.