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It Isn't The Boat So Much
Okay, this ought to be right up my alley. But before I get started I need to mention all advise given above is spot-on. Size matters, intended use matters, and generally speaking multihulls have inherent advantages over monohulls.
Okay, here goes. Due to a nasty fall at the age of three I became partially paralyzed on one side. Among other things I lost most of the use of one hand. You could say I am one of those singlehanded singlehanders (there must be others).
From the point when I started to learn how to sail and the 35 years since I've been aboard and underway on countless designs. Through that experience I am fairly aware of things that make life easier underway. Which brings me to a fundamental statement: IT ISN'T THE BOAT SO MUCH AS IT IS THE SYSTEMS. Let's face it, we are all handicapped underway. Even the most physically capable sailor requires some sort of mechanical advantage, design consideration, other specialized set of tools, and a fair bit of planning to succeed.
Here is a case in point. I currently singlehand a 30' catamaran most times she is underway. She is of no known pedigree (home-built, one-off design) and when I bought her she was unfinished. I knew even then I could make her user friendly, though. On a boat this size self-tailing winches are almost essential for me if I'm not using the self-tacking foresail. But when on a simple daysailer all I need to do is tie the ends of the jib sheets together. I'd benefit immensely from roller furling, but it isn't in the budget right now; the stability of the cat makes going up to the foredeck so easy it doesn't matter much. While I'm up forward I can either secure the tillers or employ the autopilot. While I can do it, a lot of hand-over-hand action under tension isn't my strong suit; and so, I installed an electric windlass.
There are countless other ideas I've incorporated into my current boat, but I'm still sipping on my first cup of coffee and am a bit foggy at the moment. Really what it all comes down to is a matter of forethought. Trial and error plays a part, too. Yes, I've had to re-work a few of my systems. While I appreciate the OP may be asking for the best design for the purpose, I think finding a boat in good condition and modifying it to suit makes far more sense.
Last edited by Michael K; 04-04-2010 at 10:23 AM.