How Did You Learn To Do Maintenance?

[westwinds]

My stepson is considering a 31 to 36 foot sailboat and his question to me was how do I learn about doing repairs? I cannot advise him because my father, who was an automotive machinist, taught me a lot as a kid, and I have worked as an electronic technician so with books about boat repairs, say from authors like Don Casey and Nigel Calder, I feel like I can do alright with sailboat repairs, but what about the person who did not have any background but is intelligent enough to read and understand a book? How can he make the jump to working with tools to get a job done? I would like to hear from folks here who have made that transition from books to tools and how did you go about doing it. What were the problems? Did you get training somehow?