Posted on behalf of Richard Hudson:
Excellent information in this forum topic! I must say that I do like Andrew Evan's book, which I have read a few versions of over the years. I like that he has a humble and analytical approach, and think there is much worth reading in his book, even if one is not racing.
As David mentioned above, I would emphasize the importance of really knowing how to handle all the sails on one's boat, solo. That's quite boat-specific, and I think most boats will need some kind of modification to get systems to work well singlehanded. It may take a lot of sailing one 's boat to fully figure out how to handle it effectively solo. For instance, it took me a long time to realize that if Ivery loosely tied a rope around the end of the spinnaker pole to the lifeline or pulpit, then I could manage connecting/disconnecting the mast end of the pole much more safely and easily.
I got into single-handing because I couldn't find crew to leave Argentina with. I was fortunate in having met some singlehanders who gave me advice and encouragement. Most of the time, I still sail with crew, but I've come to enjoy single-handing more and more. It can be a really powerful and positive personal experience. I wasn't an OCC member when I started singlehanding, and didn't know of David's timer. Searching for a clockwork kitchen timer was a culturally interesting experience in South America, where time seems to have a different meaning :). I couldn't find a kitchen timer in Argentina, Uruguay, Brazil. I was able to buy digital alarm clocks. The trouble with digital alarm clocks is when you've just woken up, looked around, want to set the alarm and get back to sleep, and the next 20 minutes (or whatever time you're using) takes you into the next hour. The simple math of adding 1 to the hour to set the alarm on a digital clock is surprising hard to do correctly just after waking up--I frequently got the hour wrong and overslept.
Drinking a large glass of water before going to bed will wake you up after a while if you don't have an alarm (but it's much better to have an alarm). I think the boat most people will singlehand is the one they own. My 50 'staysail schooner is not an ideal singlehander's boat, but it serves. Whenever it is gusty and I'm doing frequent sail changes, I think a lot about how much easier a junk rig would be.
I also appreciate David's point about headsails being undesirable. My jib's roller-furler failedmid-Atlantic on my last singlehanded trip and it was a pain raising and lowering the jib with all the friction in the roller-furler 's foil. I found myself delaying raising the jib and dousing it very early--making for as lower passage--due to the troubles of handling it.
I definitely agree with David & Tony that having both a reliable autopilot and a windvane is best. The autopilot that came with my boat gave me no end of trouble, so I discarded it and just use the windvane and then sheet-to-tiller when the wind is too light for the windvane. This makes me hate motoring even more because I have to hand-steer to motor :). Some day I will get a good autopilot. If one doesn't have both a reliable autopilot and a windvane (and even if one does), I think that learning how to do sheet-to-tiller self-steering is really worthwhile. Sheet-to-tiller isn't good for sail changes and is much less convenient than a windvane, but if the windvane is broken, at least you can keep sailing instead of having to heave-to while you fix it.
---this email is from: Richard Hudson
Vice Commodore, OCC