It is the same as Spork's cart. Off the ground, the tailwind turns prop CCW from the rear. Wheels turn into the tailwind. On that basis, I would expect the cart to move to the left..
That image just shows the normal rotation of the propellor and the wheels, when not the cart is not on the ground.
The cart moves to the right, if there is a force on the cart that is greater than the CCW torque from the rotor (turbine). That greater force is the sail force on the cart and prop, driving it downwind. (Configuration A).
When it's on the ground, the cart should move off to the right, relative to that image, if the wind force can overcome the rolling friction.
The propellor and wheels will then be moving in the proper direction to get to wind speed.
Upwind carts are the same configuration, but designed so that the turbine force, is greater than the downwind sail force, so they move upwind.
This configuration produces failed upwind carts that point downwind, and are driven downwind by sail force.
If the wheel rotation is reversed, then the cart moves downwind driven by both the CCW turbine torque, and the sail force. (Configuration B)
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As for any "record" I don't expect that at all.
I want to see the driven cart when released, and moving as fast as it can, -not- be caught and passed, or paced, by the freewheeling prop cart.
If this never occurs, then....
I would expect that Configuration A will be the slowest at all times.
If the gearing allows a better power match to the tailwind, Configuration B may be faster off the mark, but the free-wheeler will have the highest top speed.