So will headwind induced 'free' airspeed come into play?
There is actually a way to use the "free" energy from wind, but not in the way you seem to be thinking...
I fly a lot of RC, and sailplanes (thermal and slope) in particular (but also have a lot of warbird and aerobatic biplane experience).
To use the wind as an energy source requires being in flight already (not taking off, so to speak), and while at flying speed passing from a lower-speed wind layer into a higher-speed wind layer (which will give you a "temporarily" higher airspeed; for "free"). If you continue on the same heading / AoA, you'll slow and lose that speed; but if you instead continue to pull up and over the top you can maintain that extra airspeed and begin flying downwind, which will then give you the effect of that higher airspeed added to the downwind speed. When you then complete your loop , and simultaneously break back through the lower-speed wind layer you'll be back at the "starting point" but will arrive there at a higher airspeed than you began. You can repeat that looping flight, continuously passing from the lower-speed wind layer into the higher-speed wind layer (and gaining airspeed each time you that), and maintaining that gain in speed by turning downwind and dropping back into the lower-speed layer... Each time you do that you'll go faster, and faster, and faster, and faster; gaining "free" energy from the wind.
Kind of neat, and lots of fun! Look into "dynamic soaring"... For an rc glider that will generally fly at less than 30mph in a level glide, the speed record at this point is in the neighborhood of 450 -500mph. Not too shabby for "free" energy.
Of course, as the others have mentioned this won't work as an assist for a climb to altitude test; it's not a method to "cheat", but it's fun never-the-less. Birds of prey have been using this method for millennia; humans are really just getting started with it.
