Single Handing Features
A boat that's set up for singlehanding should have all lines led aft to the cockpit, self tailing winches, easily adjustable main sheet, autopilot, roller furling jib, and the main should be easy to reef while underway. Originally you said a boat in the "30s" and my '88 H-35 is very easy to singlehand. I've sailed over 10 knots and flown a spinaker all singlehanded but I admit this is probably pushing the envelope but it's an example of what can be done if you're properly set up. Heck, look at Ellen MacArthur and her recent round-the-world race in an open 60!In the cockpit I'd look for a jib sheet winch that is easily adjusted with one hand on the wheel and the other on the winch handle. I sit on the lee edge of the cockpit while steering and can easily tweek the jib sheet.Tacking must be easy too. With the main sheeted amidship, or with the traveler lines in their cam cleets, I can flip the jib sheet off its winch just as the boat is passing the eye of the wind and quickly take three wraps on the lee winch and take the slack in. A few turns on the winch with the winch handle and she's tight enough to sit down again and it's back to business steering and tweeking. One trick is not to pass the eye of the wind too fast so the new active jib sheet isn't loaded up.Make sure there's nothing for the jib sheet to snag on when coming about. Also, don't use a "deck sweeper" jib - get something with a high clew for good visibility (hummm four "eyes", that's appropriate!).When handling the main, reefing or taking it down, an autopilot is a must. I have the Dutchman system so droping the main is really easy single handed.The biggest problem I see with singlehanding is finding time for boat maintenance, maintaining a household, working, and finding time to sail! Having said that, my neighbors 20 year old is attending college full time, works summers doing brightwork and polishing, and just bought a really neat but older little Catilina 23 (or 22?), white deck and coach roof with a red hull. Last summer she played musical slips while moving it around the marina when someone was gone. And she dosen't even own a car! This is all about priorities in life. Where there's a will there's a way so follow your dream!