I've single handed 15 to 26 footers. The latter was a 26 ft Knockabout. A real sweet boat to handle. No auto pilot, Just me the boat and the wind. No real problems at any time.
Now thinking of getting about a 40' or better to live aboard and single hand. Will definitely have a wind vane or electronic Auto pilot. Due to more boat and much larger sail area.
One of my tricks single handing was to plan out everything first and practice, practice and again practice.
Still like motorcycle riding. You need to have a very healthy respect for the sea & weather. As a biker has that healthy respect for the road.
Get cocky and you are dead meat.
