Originally Posted by CherokeeSailWench
Basically, what questions should I ask of a potential instructor?
Why do you want lessons? So you can sail the boat you own now, charter boats, buy a boat in the near future, crew on someone else's boat, take your non-sailing wife and kids out, sail by yourself singlehanded, 15', 20', 30' boat?
I wanted to learn how to take my friends and family out on 22-25' charter boats from a club rather than own my own boat. In that case, the club was more important than the instructor. Two months later now I've met and sailed around three of their instructors so far and feel very comfortable I got my money's worth. They also ensured I was ASA certified so that I could charter boats from other clubs around the world.
As an inexpierenced sailor, there isn't much you can ask a potential instructor that will increase your chances of getting a fair deal. I would just make sure you're getting instruction from an ASA or US Sailing certified school and let them assign you the instructor. Pick a school that has multiple instructors. Many schools will let you retake portions of the course for free if you desire.
My club has 1-2 classes sailing almost every weekend. So if I wanted, I could join a different instructor later for free I think.
Hope that helps.