Meteorologist learn a lot of theory from books and articles and comparing your forecasts to reality. I also I think I have learned much about very local wind idiosyncrasies from driving and hiking around the terrain that impacts the wind velocity and direction.
But I have learned the most by talking with people who actually use the wind in a given locale.
The conversation below illustrates this very well. In single thread I learned more about the wind quality at Lake Isabella and about a sensor issue in Maui, Hawaii.