His unwillingness to be more forthcoming with information concerns me. How the hell can you even begin to recommend a boat when you don't even know whether he is planning to go as a single handed novice or with a paid crew of experienced people?

You may be right, he may be a troll. However, if he is a newbie and just embarrassed that he doesn't yet know enough to ask the right questions, I don't want to just turn him off. We were all inexperienced dreamers at some point. In my case, if my wife hadn't asked my that one life changing question, I would still be just a dreamer. Her question? "Why can't we?" Asked as we were driving home from a farewell party for some friends heading south and after I had said "Man, I wish we could do that!"