I wonder if they still teach the Heisenberg uncertainty principle? From my astrophysics days essentially you can know the speed of something fairly accurately but the position is quiet uncertain. The opposite is also true. Yeah ok...too much red wine! But back the question, yes you even understand yourself by knowing the angles are different. So headwind, higher angle (or height) with less horizontal distance. Conversely, with tailwind lower angle (height) with greater horizontal distance. Thus h/d is the same.
With regards to speed, I suggest you look at the different types of speeds. There are a multitude of types IAS, TAS, GS, CAS......etc etc etc