I've avoided these discussions thus far - I find them confusing force and energy, and the use of a boating analogy to people who have never sailed (I know that's not you,
@anorlunda ) isn't helpful. I also think treadmill analogies are not helpful either.
I maintain that thinking of this in terms of wind energy is unhelpful, because with an infinite volume of air, there's an infinite amount of energy that can be extracted from it. (In real life, replace "infinite" with "very large")
1. Consider a cart with a sail, going exactly as fast as the wind. Do the wheels have to be frictionless? The answer is no, the requirement is that the thrust from the wind is equal to the drag from air plus from the wheels. If I have more wheel friction, I need a larger sail, to be sure.
Agree?
If you think you understand, answer this: You are riding in this cart at the speed of the wind, and the brakes are partially engaged. What happens when you release the brakes? The answer is - nothing.
2. Consider a cart with a sail, going exactly as fast as the wind. A battery-powered fan is mounted on it, to move air from the front to the rear, but avoiding the sail. The fan is switched on. What happens to the cart? It accelerates forward.
Agree?
Our cart is now going downwind faster than the wind. No problem here - it has its own power source.
3. Now we put the two together. The wheel brakes are taken from a Toyota Prius, and so generate electricity. I remove the battery and use this electricity to power my electric fan. And there we go.
Of course we can then replace the electrical system with a purely mechanical one.