
I don't consider that "counter-intuitive"
The guy making that bet wasn't thinking.
The wind is not pushing the vehicle, it's spinning a prop that provides energy to a drive train. This vehicle should be able to drive straight into the wind too (reverse the prop for that).
As for the sailboat thing, I got tired of that article right away. I could do the entire explanation in just a few sentences.
Air has mass and inertia. When the boat is sailing crosswise to the wind, the sail is positioned to force the air to change course. The inertia of the air hitting the the back side of the sail pushes against the sail. The mass of air flowing across the front of the sail is also forced to change course, and its inertia causes a partial vacuum on the front surface of the sail, which pulls the sail forward.