I envision the near future of space flight to be like the airline industry and I think that in Pioneer that would also be true.
This means that human pilots are required for at least three reasons:
1. Any technology made by humans is going to be flawed and break. This includes AI and automated systems. There is a series called Mayday on YouTube that documents airline aircraft disasters. The number of times an automated system fails is quite high, and many passengers would be dead if not for the skills of an experienced pilot.
2. Legal systems progress much more slowly than technology. Liability and not technology is why we do not have flying cars. 30-40 years from now we still will not have a legal and regulatory framework for flying cars let alone people jetting around on autopilot in near earth orbit.
3. People trust people and not technology. Ask any airline passenger if they want to fly in a fully automated airplane (Which is possible today), and the answer is not only no, but hell no.
30-40 years is many generations of technological progress, but is less than one generation of human progress. If we are 'progressing' at all. There are people still living today that remember a time without TV, Cell Phones, Personal Computers, and the Internet. Many of them are still in charge. Let that sink in for a moment.
30-40 years from now, there will still be people in charge who remember a world without Space X, Blue Origin, Cell Phones, and the Internet.
There will still be pilots in space for at least another 100-200 years no matter how much technology progresses.