[DominikR]

Once travel into space is viable for average tourists (not only tourists willing to pay 100 million dollars) it'll probably also require more pilots than today, so I'll say that he still has a better chance being there before you.

[AndrewKemendo]

When I made the bet with my friends, predators/reapers were just starting to come online and it was clear to me that they would be the wave of the future and eventually pilots would be out of the loop.

We certainly aren't there yet but my long term bet is that humans will be pushed further out of the loop for all things transportation - space travel being one of the main ones I would expect to transition first as it's basically there today anyway.

[DominikR]

At some point in the future: Yes. But there's no way that this will start without at least human backup pilots on board.

And then there's the testing phase where many pilots will be needed to validate the safety of such flights.

Even when you look at various private space travel companies you'll find that they plan to use human pilots. (Virgin Galactic and others)