sailordude, There are those who can not hear and there are those who will not listen. You just listen with your eyes but you do listen. I think that for many people a lack of exposure can lead to asking questions that are completely obvious to those that grew up in a world of considerable diversity. Farm kids know more about handling rope than city grown kids just because it is a part of their everyday life. They know about the things in their world that will harm them because there are so many on a farm and they are constantly exposed. Firearms, fuel, tools, large animals, moving machinery, working in and around tall barns with no guardrails teaches them to be aware of their surroundings all the time. They grow up with stories of neighbors who let their guard down for a second and were killed or crippled.
I think that you and your buds would benefit greatly reading contempory stories by sailors and about the sailing world and the successes and failures that are so informative. In addition to the basic "how to sail" books there are wonderful stories about real life and real people and the screwups they admit and the grand successes that they have enjoyed.