I used this model to help understand it, years ago:
The large central wheel has traction with the ground. (The two smaller wheels just to keep it from tipping over.) The cart travels from left to right, with the central wheel turning clockwise. If you held the cart off the ground, and turned the main wheel clockwise, the parachute would move right to left, toward the rear of the cart.
Now,
disregarding all wind, think about the cart in motion and convince yourself of the following four things:
1. When the cart rolls along the ground, the parachute is moving right to left
relative to the frame of the cart, just as it would do if the cart were held off the ground and you turned the main wheel clockwise.
2. When the cart rolls along the ground, the parachute is moving left to right
relative to the ground. So relative to the ground, it's moving in the same direction as the cart, but not as fast (about one third as fast).
3. If you were to push on the parachute toward the right, say with your hand, it would propel the cart toward the right, because of fact 2.
4. But because of fact 1, as you continued pushing on the parachute, the frame of the cart would be propelled relative to the round faster than your hand is moving. About three times faster.
Now imagine if it were a wind, blowing left to right, pushing on the parachute instead of your hand. Like your hand, that would propel the cart forward (fact 3). Suppose the wind pushes the parachute to two thirds of the wind speed, which it can do because the parachute is still slower than the wind. But (by fact 4), the frame of the cart would be moving left to right three times that fast, or twice the wind speed.
In principle, this would work. (In practice, not so likely, because there would be friction in every important part, and it can only travel until the parachute reached the pulley at the rear of the cart frame... unless there were more parachutes mounted at intervals around the cord, furling themselves at the rear pulley and unfurling themselves at the front pulley, which would be an even bigger mechanical nightmare.)
So, how is this like the Blackbird? The parachute represents the rear surface of the Blackbird's propeller at some (any) particular point in the area the propeller sweeps. Not, please note, a specific point on the propeller itself that spins with the propeller, but a particular point in the propeller's plane that's fixed relative to the cart frame. As the propeller sweeps past that point, the propeller blade rear surface at that point moves (because of the propeller's angle and spin) left to right relative to the ground -- fact 2 -- so that the wind pressure at that point will propel the cart left to right -- fact 3 -- but at the same time, that intersection point is moving right to left relative to the cart frame -- fact 1 -- so the cart frame is moving left to right faster than the rear surface -- fact 3 -- so if the rear surface is moving close to the speed of the wind, the cart frame will be moving faster than the wind -- fact 4.