One of the hardest parts of this video to wrap my head around was the notion that while there is a 10 kt apparent wind from the stern, the boat is moving backwards relative to the ground and stationary relative to the water, until it accelerates past the current speed. Once the boat starts moving up river at a 10kts over the ground, then it will be stationary relative to the ground with the river flowing past. Since the wind speed is 0 relative to the ground, the boat will become becalmed, the apparent wind drops to 0.
I just don't see how the boat could move upstream under those conditions. I can see that the boat could sail back and forth across the river and not move down stream, but not move faster than still air.