Size doesn't matter
I started on a Catalina 30'. It had all the sailing bells and whistles, hanked on reefable jib, floating goose neck, 3 reef main, Cunningham, whisker pole...... and only the main jib sheets operable from the cockpit. After reading Chapman's Piloting I found myself very well prepared for everything I ran into. She did not have a knotmeter, GPS, or autopilot and the depth meter only worked when the water was over 30' deep. I consider most of my sailing to be single handed as the admiral just likes to be seen on the boat not actually help operate it. I could never get her to preform in light winds as I could not tell if any of my trimming was having a beneficial effect on the speed. Once I bought a GPS/depth sounder sailing became much more interesting as I could actually see what effect the sail trim was having on speed and what the bottom was doing. Needles to say we arrived late at most of our club events and ran aground EVERY single time we went out. After building an 8' hardshell sailing/rowing dingy (mainly for the dog and his mandatory trips ashore) I really learned about sail trim and how it all interacts.What I learned from this is that:It really does not matter what size boat you learn on as long as you can physically handle herAn autopilot goes a long way toward making any boat single-handableSmaller boats give you a much better feel for sail trim/boat speed interaction.Larger boats give you the capability to experience a wider range of wind/sea conditions with out undue danger.Smaller boats are more excitingLarger boats are more comfortable (on and off the hook)I'd recommend a boat just large enough to anchor out in so you can see the sun come up on the water and so you have at least a jib and main so you can experience working with all the sail controls you find on a larger sloop. For a family of 5 that was a 30' for us.
I started on a Catalina 30'. It had all the sailing bells and whistles, hanked on reefable jib, floating goose neck, 3 reef main, Cunningham, whisker pole...... and only the main jib sheets operable from the cockpit. After reading Chapman's Piloting I found myself very well prepared for everything I ran into. She did not have a knotmeter, GPS, or autopilot and the depth meter only worked when the water was over 30' deep. I consider most of my sailing to be single handed as the admiral just likes to be seen on the boat not actually help operate it. I could never get her to preform in light winds as I could not tell if any of my trimming was having a beneficial effect on the speed. Once I bought a GPS/depth sounder sailing became much more interesting as I could actually see what effect the sail trim was having on speed and what the bottom was doing. Needles to say we arrived late at most of our club events and ran aground EVERY single time we went out. After building an 8' hardshell sailing/rowing dingy (mainly for the dog and his mandatory trips ashore) I really learned about sail trim and how it all interacts.What I learned from this is that:It really does not matter what size boat you learn on as long as you can physically handle herAn autopilot goes a long way toward making any boat single-handableSmaller boats give you a much better feel for sail trim/boat speed interaction.Larger boats give you the capability to experience a wider range of wind/sea conditions with out undue danger.Smaller boats are more excitingLarger boats are more comfortable (on and off the hook)I'd recommend a boat just large enough to anchor out in so you can see the sun come up on the water and so you have at least a jib and main so you can experience working with all the sail controls you find on a larger sloop. For a family of 5 that was a 30' for us.