I am afraid that I don't understand your point. With regards to the first partial quote, of course, it is hard to say whether he will ultimately like this boat better than some of his other options at the time. My only point in that sentence was since he has little or no experience with boats of this size and type to which to compare the Bristol 29.9, some of the other equal or less expensive options which were better equipped, better maintained and upgraded, and more rounded designed boats to begin with may have worked better for him in the long run. I did not mean to suggest that he would not enjoy his boat.
I don't know ho wmuch you know about this fellow or the process we went through but over a fairly long period of time, I acted as a sounding board for this Gent in his search for a boat that met his needs. I provided second opinions, clarifications, references to other sources of information, copies of original literature, and alternative suggestions in response to a long list of questions. I met and looked at one boat with him that he had concerns about.
He and I went through a long process not all that dissimilar to the process that I have gone through with dozens of other folks, sometimes as many as a dozen a year, some of whom like Willaim who had some experience, but not a lot with the boat type in question, and others who are just plain new to the sport.
It was a process in which literally a several dozen boats were considered from perhaps 10 to 15 manufacturers. Over the course of his search, we discussed Willaim's goals and preferences in great detail. We exchanged ideas on items that he had read. We discussed theory and particulars. We discussed things that could be done to optimize some of the boats that he was considering and the relative costs involved. We discussed the good and the bad news on each boat, both from his viewpoint and my own experience. Ultimately, we narrowed his search down to five or six boats and he bought one of them.
Along the way, between, his readings, and discussions with me and others, I think that the fellow in question learned a lot and refined his goals, expectations and taste regarding what appealed to him visually.
I consider this a very successful process all around. I enjoyed meeting William and helping him along in his search. The process eliminated boats that probably would not have suited his objectives very well, such as the Bristol 32 or a Vanguard. The process ultimately steered him to a decision that I think was a reasonable one. The fact that the boat he bought wasn't the boat that I would thought better suited him is irrelevant from my point of view. He was buying the boat not me. From the criteria that he had given me, all of the boats on that short list were good boats in their own way. That seems appropriate to me. (For what it is worth, as he voiced them, his goals and criteria for sellecting this boat are very different that my own would be if I were buying a boat of that size and budget and so almost none of the boats on the list would have been a boat that I would buy for myself, they seemed to make sense for him)
I never, ever claim to be a mind reader. I listened to what the fellow told me and I made suggestions. The gentleman in question had very pragmatic concerns and so from a pragmatic point of view his choice made less sense to me than some of the other choices, but as I said at the start of the sentence that you chose to partially quote, "we all buy the boats that speak to us", and "the Bristol 29.9 clearly spoke to the gent in question". I don't see the problem.
As to your last point, in the last email that I had from William, we discussed me joining him for a sail; to coach him how to sail the boat short-handed and perhaps look at options to improve the boat for single-handing. Unfortunately I became quite ill about that time which cut into my sailing time around the time that he bought the boat so it hs not happened as of yet. I still hope to hear from him again, to see the boat, and to do some sailing together.
I just don't see where the problem lies.