I was 26 when my dad bought a Columbia 45. It was 1977.
No furling, no windlass, no instruments but a compass. He purchased depth and speed which I installed. And we put in a VHF. Several years later he bought a LORAN.
Soon after he bought it, he invited a friend and his son aboard, both experienced sailors, to teach me how to sail. The lesson lasted about an hour. After that I was on my own because my dad assumed I knew everything there was to know.
My first single handing experience was about a month after he bought it. I remember locking the wheel, running forward and hoisting the main then running back to the wheel and correcting the course. Then I headed it into the wind and ran forward again and hoisted the genoa (I had hanked it on prior to going out) then running back to the wheel and fine tuning the sheets and outhaul.
One of my proudest moments was when tacking. The wind was about 15 knots that day. I turned the wheel, locked it, released the starboard sheet, hauled in the port sheet and just as the wind caught it, I cleated it. It was perfect! I didn't have to trim it at all. The only problem was there was no one to witness it.
Later I found out my dad's friend and his son were out sailing and saw me. They later told my dad I "looked pretty good out there."
For the next eight years I singlehanded that boat most of the time. Everyone who came on board saw themselves as guests and the idea of doing any work never crossed their mind.
I often joked I was the only single hander with a crew.
The three most important things in single handiing a boat are planning, planning and planning.