Pilotless planes won't happen for a very long time. It will come down to cost. A pilot will be cheaper than designing in sufficient system redundancy for pilotless planes. It will also be heavier, all those systems, a pilot, relatively speaking is pretty light.

All that tech comes at a cost, and at least for the forseable future, pilots will be cheaper. IF one tries, you also have to account for the additional certification costs that the FAA will certainly require.

I don't believe you can efficiently retrofit a current design, so it will have to be a clean sheet design with all the systems integrated. Boeing can't get a new design done in less than 15 years now. How long do you think it will take the FAA to come up with regulations to cover a commercial-passenger clean sheet design?