Earlier quoted context omitted.
The people-mover has to expend more energy to push you because you're applying a stronger drag force, so energy is conserved.
Okay so in this case the people mover is drawing the additional energy. Additional energy is being provided from somewhere i.e a diesel generator somewhere up stream has had to increase her fuel consumption to maintain the power on the network.
But then increase the rolling resistance - the generators on skateboard wheels -- but you still, by drag, move at the wind speed, you're just stealing more energy from the wind/peoplemover now.
Then you use that energy (simply by a chain linkage) to spin the propeller, blowing air aft. The propeller pushes air backward, changing the speed of the air molecules in the region behind the vehicle from whatever they were moving at, e.g. 10 knots relative to the ground, to 0 relative to the ground. That energy pushes the propeller and with it the vehicle forward, by Newton's 3rd law. This is the second electric skateboard driving forward, in the frame of reference of the peoplemover.
So now you're moving faster than wind speed, in the direction of the wind, stealing more power from the airstream (peoplemover) than you could steal by the (original) drag of your craft alone. You got there by increasing your rolling resistance, which won't slow your craft until the rolling resistance exceeds the available force from the wind. In the analogy, this would be equivalent to jamming your brakes so hard against the floor that you stop the peoplemover rail from moving at all. You use the extra energy -- the amount being spent by the wind to counteract your increased rolling resistance -- to push yourself faster forward.