Capsize, TF, spouses & bigger boats
It is funny, but it has generally been my spouse(s) who wanted the bigger boat. They have usually wanted a little more comfort and in this latest case the ability to bring another couple along. I really liked the size of my 28 footer for the ease of single-handing and in doing things in general.
That said, as I am getting used to and getting some of the bugs out of my current boat, I find that its not that much harder to single-hand my current 38 footer than my previous 28 footer and that in some ways it offers a lot more convenience albeit at the expense of using more sophisticated electronics and bigger hardware.
The thing that I have noticed is that with far greater frequency than the past, people who are just getting into sailing want to start with bigger boats and see their first boat as their ultimate boat. Maybe this is just me but, I just don''t get it. It took me nearly three years to research what was out there in the size range I was interested in and to get sails on or to talk to owners of sisterships of models I was considering before I was certain which was the right model for my needs. I don''t understand how someone who is just learning to sail can make a reasoned and informed decision on a bigger boat. I am not putting anyone down here but it sure is a mystery to me.