[takes a deep breath]
you can ride downwind faster than the windspeed, and it will feel like a headwind. you are moving through the body of air, and will feel resistance.
to put some numbers on it… say wind speed of 5mph, cycling speed of 15mph. if you cycle in the opposite direction to the wind it will like a 20mph headwind. if you cycle the other way it will feel like a 10 mph headwind, even though you are cycling downwind. you’re overtaking the mass of air by 10 mph, so get some drag from moving through it.
also as far as i’m aware, drag from wind resistance depends on the square of the wind speed, so at 20 you get four times the drag you do at 10. you lose more into a headwind than you gain in the tailwind!
with the land yacht thing, they can go faster than the windspeed, but only across the wind (at least some crosswind component), not directly downwind. when you’re going crosswind the windspeed and the groundspeed of the yacht add up (vector additon) to give more airspeed over the sail, hence ***zooooming*** crosswind…