I stumbled over this web-site and I have been busy reading since last week. There is certainly a great deal of material here!
My wife, Aimee, and I are moving to the Caribbean in a couple of years and I have been toying with the idea of getting a boat of my own. I have been sailing for only a couple of years (and brown-water mostly, as well) amd I consider myself mostly a rank novice despite the fact that I rec'd a license to sail a boat myself.
I have joined a club where I noticed there was a particularly concentrated assortment of older fellows who tend towards wind-power and prefer actually sailing to simply bbqing in the cockpit of a $500K boat that has never left the harbour. From crewing for them, I am getting some experience with different hulls and sail plans. Given the limited water in the area, most of the boats are still rather small and I feel that this is a real blank spot in my education (anything over 30 ft in length).
The club also has a "sail share" where each season you can buy into it and take any of its Tansers or Sharks out for the day (and not be bothered with paperwork!). This serves me well, because it also gives me the option of sailing with other, like-minded people.
So, I am slowly building my experience with different boats. This forum is great for that as it has already given me a few ideas. I had given up on ever owning my own boat, particularly in light of the need to set-up and maintain a business in a couple of years time. My education, although fairly good, won't really help me down there so I am still thinking about different opportunities. Adding a boat to that did not seem entirely viable. But having read a bit, and talked to a few people, I am almost certain that I can afford a smaller day-tripper. Although I am green with envy at seeing some of the really fine boats that the community here can boast of, I know those are out of my range. But then, I am not sure I would ever really need something that I could sail the world with - a weekend would be fine, I am sure. And we can talk again in 25 years...