My dad, the designer, believed that something about 28-33 ft was the 'perfect' size for a boat. This was the philosophy behind the Raider 33, a boat I have called 'the holy grail' of cruiser-racer boats, because it is fast, beautiful, roomy enough, and seaworthy. You could singlehand one easily (probably better off without the tall rig) and live on it as long as you'd like. The R33 (or possibly the H30, being about the same in interior room) is the only thing I would consider as a step-up boat from my H25.
In 2008 the editor of
SAIL wrote an editorial marveling at how the length of the average new boat and the age of the average first-boat buyer were both approaching the same range: 50-55. He went on to extol all the virtues of electrical gadgetry, push-button furling, winches, etc. I was reading this on a lunch break at West Marine and got nauseous. Then I observed that the biggest, flashiest ads in the same issue were all for boats above 45 ft. And then it was clear to me.
Chichester famously said (and rightly) that 'the usual condition of something electrical on the boat is not working'. I'll say this: if you are considering an 'ideal' semi-retirement/singlehanding/liveaboard/LT-cruise boat, and you need a lot of electrical junk to sail it, anchor it, furl it, reef it, monitor and inspect it, and dock it, you are looking at too big or too complex a boat. I won't deny that Dodge Morgan's hedonistic RTW adventure bored me. He video-taped Cape Horn and then went down to take a hot-water shower, run his laundry, microwave some dinner and chat on AOL. I mean really! How could you
NOT be successful when you have a $1m 55-footer with another $1m in gadgets on it? That's not sport or a hobby; that's living in a condo in Manhattan. He could've done that on a cruise ship. And then, whatever would happen if it all broke somehow? Dodge would probably have phoned for support and a chopper would have shown up with three techs and spare parts within 4 hours!
Not for me. Give me a smaller, simpler, more fun boat any time. So I much prefer hearing from people like Robin Graham, or that guy with Atom, than from the guy on YouTube with the Beneteau 49 who complained (in between taking hot-water showers and running the dishwasher) the 65-ft bridges on the ICW were too low for his mast. Boo-hoo!