Here are a few tips.....
John, I single-hand about 80% of the time on my C 27. It is essential that you be able to leave the helm for short periods of time to make adjustments, get your jacket, use the head...whatever. You should have a wheel locking device to hold course temporarily. Whether you do or not, I highly recommend you install an autopilot, I wouldn't go out alone without one. On a C27 the primary winches should be close enough to the wheel to steer with one hand and release and pull in the sheets with the other. Cam-cleats will make your life easier. You don't really need to start winching (with the handle) until you get the course set, that is when you lock the wheel, insert the winch handle and trim. An autohelm with a tacking feature really makes this a breeze. I have tiller steering and often, especially when jibing, I stand with the tiller between my legs, steering with my knees, leaving both hands free to work the sheets and bring the boom across, etc. As to the halyards, raise the main while under power with the wheel locked and the boat pointed into the wind. Hank on the jib at the dock, but don't raise it till you get to the sailing area. Once there, bear off to 30 deg apparent, lock the wheel, use both hands to haul up the jib, then the winch handle to trim. Sometimes, after hanking it on at the dock, I will lash the jib to the lifeline stanchion with a slip-knot. This trip line is led aft to the cockpit. That way it stays secure on deck till I'm ready to hoist. When dropping the sails, being able to leave the helm is paramount. Since I must go forward or get on the cabin top for this, I look for a calm area inside the harbor. One more thing, know how to get back in the boat if you fall off. Good luck, plan ahead and be careful.
