Have you read any of the many books on sailing tactics?
Years ago I got Eric Twiname's, "Start to Win". I read it once to get an overview of his theory of sailboat racing. I then read it again and tried to remember situations that the varous topics applied to. When I finally started to understand what he was saying, I could see the words from the book as a race unfolded.
Stick with one author so you are not distracted by the different words that each author uses to describe a particular situation.
How do you get to Carnigie Hall: Practice, Practice, Practice.
How do you get to the Pocono's: Quit Practicing.