single handing tips...
Tommy, you're pretty much ready to go... although I recommend a small autopilot if that's in your budget. You can lock the tiller with a couple lengths of rope or bungy, but an auto pilot will offer you that and so much more.Very important... buy a harness and tether, and wear it. I always wear mine when singlehanding, and I clip on as soon as I leave the slip. You don't need to rig jacklines for a daysail, it's easier to use a few secure points on the boat. I clip on to an windward, spare jib car or you can mount a folding padeye in the floor of the cockpit. Anyplace secure, that will allow you to reach everything in the cockpit. Staying attached to the boat is rule numero uno. I put the PFD on if the weather pipes up.. but hey, I'm in San Diego, how often does that happen. I often steer the boat standing up with the tiller between my knees, leaving both hands free to handle the lines when tacking or hoisting/dropping sails. It's nice having ST winches, I don't on my C27, but on any boat under 30 feet you shouldn't need them when sheeting in on a tack. If you stand when you tack you'll easily be able to cast off the old sheet abd tail in the new one by hand with a couple wraps on the winch drum. Novice sailors have a tendency to leave the handles in the winches, especially the ST type, so get in the habit of taking them out when you're by youself in case you have to make an emergency tack. Oh, and watch for the boom if you're standing! On a jibe, grab the mainsheet tackle and pull the boom across by hand asap, then you can concentrate on handling the jib and steering. I would recommend getting an adjustable tiller extension so you can move around in the cockpit or sit on the rail. Plus, the adjustable Forespar type has a coaming mounted bracket you can slip the ball handle into to lock the tiller. My biggest fear was getting in and out of the dock by myself. Once out in the open there is plenty of room for mistakes. Anyway, keep your boat hook handy in case you get too near another boat or a piling. Take your time to examine the wind and current before leaving the slip. The first time I got someone to watch me from the dock just in case. After a while I gained confidence to solo. My boat faces generally into the wind at the slip so I almost always raise the main before leaving the dock. Just slack out the sheet and traveler so the sail will weathervane till you need it... one less thing to do. I don't hoist the headsail till I'm ready to sail.If you're facing downwind or down current in your slip then backing out can cause some excitement as the wind/current will want to push the boat's nose back toward the dock before you can get straightened out in the fairway. My solution to that was to back out completely to the other side of the fairway before making my turn, this gave me enough leeway to get the boat turned and moving. On an upwind slip you start your turn as soon as you can clear the dock finger, again to provide plenty room to clear your neighbors.I think you just need to go for it and pick a calm day to start. Have fun.