Originally Posted by
noglider
The lesson here (for you, anyway) is that your position makes the most difference, not the value of the equipment. Are you, by chance, thin? I'm a thin person, and headwinds affect me a lot, and hills don't. A heavy friend has the opposite observation. I think it's the surface-area-to-mass ratio.
Because I mainly commute, I don't have much experience with hills. Condition and aerodynamics are most important in my experience. When I started, I can only go around 5 mph into 15 mph headwind. Then after 6 months, I could ride 8 mph into 20 mph headwind. Then with drop bar, I can ride 10 mph; and much less tiring.