Different people get this in different ways. I can't see it being positive feedback because that opens the question why isn't it a perpetual motion machine? Or as
@WobblyElvis says, if you push it to get it started in no-wind conditions, it won't run. It does require wind to push it.
At first I didn't "get" the treadmill example but I think I do now. Remember that it is an inertial reference frame if it's moving at a constant speed (and it is). Now imagine the treadmill the size of the entire desert (or Earth), the prop cart moving forward on the treadmill is going "downwind" faster than the wind.
Another way to think about this is that
because of the tailwind, the wheels are moving relative to the ground, much faster than the prop is moving through the air. Suppose the cart is moving at 20 miles per hour with a tailwind of 15 miles per hour. So its wheels are moving at 20 mph relative to the ground, while the prop is moving at 5 mph relative to the surrounding air. Power is thrust * speed and speed is relative. If the power at each is the same, the wheels have low thrust at high speed while the prop has high thrust at low speed. This difference relies on the relative motion of the wind with the ground, thus cannot work unless there is wind. It is not a perpetual motion machine.