Great comments about sailplans and furlings - thanks guys!
How about some other issues regarding single-handing a 34-40 foot cruising sailboat?
Such as autopilots vrs wind vanes?
From what I've been able to find, cockpit mounted autopilots although common are prone to failure and below-deck autopilots are recommended. I really don't know the difference, beyond 'where' they are on the boat. But wind vanes sound less likely to disappoint, and simple is better, right?
Any comments from the old salts here?
Again, I really don't have that much experience, so you should not take any of what I am writing very seriously. That said ....
In terms of self-steering I think the most important thing, first, is to think of it in terms of a skill rather than a piece of gear that you buy. The goal is to make the boat go in a particular direction relatively to the wind. Some headings are harder to keep than others and some are harder or easier depending on sea state.
Self-steering is easily divided into upwind and downwind.
Upwind, to weather, self-steering is relatively easy. Lashing the helm seems to work on most boats and it the first thing you'll want to learn if you don't already know how to do it. Here you are lashing the helm so that the rudder has a set angle, then the boat does the rest, if it wanders too far away from the wind it'll naturally turn itself back into the wind, and if it wanders too far into the wind it'll naturally fall away.
Downwind self-steering with sheet-to-tiller gets to be a bit more complicated and you really have to think about it as a skill and not a device or set of gear. There is
gear involved, often bits of surgical tubing, lines, and various other bits and pieces, but the big thing is that you have to learn how to handle your own boat, what it does in the wind, under various sail combinations, etc, and develop the skill of self-steering with sheet to tiller. Some of it is trial and error, but once you get it, you've got it, and it is kind of like knowing how to swim, once you know how to do it then it can save your life. Like swimming where a PFD helps but isn't always required, with sheet to tiller having the right "gear" can help, but you can usually rig something up with whatever you have around.
There are other ways besides sheet to tiller that are mechanical that I am still learning about, and with certain rigs such as yawls you seem to have a few sail options that can steer the boat as well ...
Then you get into the "gear" solutions like wind vane self-steering. These will go upwind and downwind with some courses being better than others in various sea states. I like wind vane self-steering, but again, it can fail, and I wouldn't want to depend on it with my life. Knowing how to steer the boat without wind vane self-steering to me is a necessity, and then wind vane self-steering is a nice convenience kind of like what people say about roller furling. I do not currently have wind vane self steering, but I will get it on my next boat.
Then you get into auto pilots which require electricity and that is a whole different thing, I'd never want to bet my life on that ...