Interesting discussion point and for many sailors I suspect the motivation then is different from now and is directly related to factors such as work, family
, domicile and so forth.
When I was first exposed to sailboats I marveled at how clever the whole concept
of a modern sailboat was. It borrowed age old technology, coupled it to high tech engineering and offered an individual enormous "freedom" to play (sport), get away from the hum drum, learn oddles of interesting "things" from plumbing
, to navigation
and so forth, or the ability to get off the grid and travel the world. What you learn is that the more ambitious your motivations the more "hatting" you need to go for them.
So to just enjoy the wind on the water, you can do it with small sailboats and avoid all the systems' knowledge etc. And the cost is more manageable.
The more you reach for the more investment is required in money and time and knowledge. And this is a process that takes time. The most highly motivated well off person cannot but the dream and step off the dock
onto a yacht and go. So lots of sailing must take a time investment.
It's also a journey of personal responsibility and "competence". While dockside we can have others service
our boats once we leave the dock
we need to be in control and deal with it all with little help. This suits many who want to escape the mommy nature of society which makes us all so dependent on others for so many things.
Having worked at sailing offshore
to new places and lived aboard in my mid 40s my attraction to boats and sailing has never left me. I scratched an itch, but the itch is still there. Now I find myself with a different relationship to my sailing because of my circumstances. Less money, less time, less need to go over thew horizon and it's now more of a comfort zone of escape and relaxation and a zen like process of caring for my boat.
I am not totally into "messing about on (my) boats. The only thing which bothers me about "fixing" things is the expense. The actual "zen" of doing it right is richly rewarding. My sailing is mostly fair weather
in optimal conditions, the type I can reach for in a day dream (I've sailed in every condition, met the challenges and so I don't need to prove anything to myself or anyone else for that matter) I've sailed solo for a week's offshore passage
, or in the snow, in raging gales, motored through a sea of glass for days. Now I like a gorgeous day with stunning blue sky and dry crisp air 15 - 20 where I can sail a reach at hull speed
with the sounds of the sea and no deadlines hovering over me.
When life conditions change (win the lottery), off I'll go to sail to some exotic destination over the horizon. There's so many reasons to sail and circumstances determine what drives me to find the one that fits.