Great Advice John:
I am in the exact same position that Eksstetter is in. I am terrified to put a lot of money into a boat that turns out to be not what I want after learning how to sail it. So I started out taking a few courses, Basic Cruising, Coastal Navigation, and then a week aboard a C&C 360 with a very knowledgeable skipper and 3 other students. It was great learning experience it was enough to show me how much more I have to learn.
Living in Alberta we do not have the sailing advantages of Coastal BC but I have found a great way to learn and have fun at the same. I am currently investigating and looking for a sailboat and was I ask if I was interested in joining a crew racing on the weekends. I jumped at the opportunity.
It seems there is a lot of boats that require crew. The more sailing knowledge and experience one has, the more of an asset one is to the team. However, with a little sailing knowledge you can still contribute to the team and learn a lot about sailing from some very experienced people. I am looking forward to contribute more and learn everything I can.
In the meantime I am learning a lot about sailboats by listening to some great people who know what they are talking about and soon hope to own a boat that meets my family's needs and is fun for all of us.
After all I am 51 years old and had a dream to sail for some time so now I can see myself sailing my own boat and enjoying it for many more years with the people I love.
Feel Free to check out the Canadian Yachting Association’s website to see all the courses that are available and what would work for you.
Good Luck Eksstetter, and I hope to see you on the Coast some time.