Ah - that puts a different complexion on the matter :-)
Your friend was wise to be cautious. The essential difference between skippering a "small" boat and a "big" boat is that in a
small boat, things can go wrong very fast but are seldom very serious when they do. In big boats, and the bigger the boat, the more pronounced this is, things tend to go wrong slowly, but inexorably, and they are almost always quite serious when they do.
It is also characteristic of things going wrong in big boats that often one thing going wrong triggers a cascade of things going wrong, and that it can take a combination of practical knowledge derived from experience and of sheer native bloody-mindedness to get them back under control. Some people have the knowledge but not the bloody-mindedness, others have the bloody-mindedness but not the knowledge.
It is possible to enhance whatever native quantum you may have of each by sailing under a competent
skipper. It is far less possible to do so "single-handing"
ab initio
That, in my view, is a compelling reason for starting with a
small boat, something around 27 feet. I happen to dislike the
Catalina 27 with considerable passion having taught quite a number of people
ab initio on that type of boat. A boat in the same size and
price range that I much, much prefer is the
Columbia 26. If you have a chance to sail each of them, you'll divine why I hold that opinion.
Most people that were not born "upon their father's ship as she wuz lyin' to, some twenty-five or thirty miles soueast of Baccalieu" do not take naturally to sailing. Wives and
children CAN learn to like it but only under a
skipper that exudes both competence and confidence. It is, therefore, IMO, NOT sensible to try to learn from scratch AS A
FAMILY. Doing that militates against having unquestioning confidence in whichever
member of the family is to be skipper.
In my teaching days - two or three couples or families together aboard a big boat - I found that the
pater familias would often get in my way by trying to "teach" HIS wife "how to sail". That particular psychology can be enormously damaging to the entire teaching/learning
environment. Instructors have to develop a "bed-side manner" that keeps it contained while instruction lasts. A person male or female that is not yet a competent skipper and instructor cannot that.
And there you have another reason why "learning as a family" may not be a good idea.
All the best :-)!
TrentePieds