Eventually, you will find that you can't resist the urge to sail and if it means singlehanded, you will do it ... so you may as well get started now! The first attempt will probably feel a little shaky, but you will soon be doing it confidently.
Obviously, the stronger the wind you are dealing with, the greater the difficulty. Start out on a day with a reasonable breeze, enough that you actually have to manage the boat.
First, halyards led aft make it much easier and safer. I manage without an autopilot or even a brake, but my boat is smaller so that may make a difference. I just use a bungee to center the king spoke. It keeps the boat going in pretty much a straight line but it will drift, so I have to allow myself the ability to correct the course with the wheel. It's easier than managing a tiller, in this instance, I think. I merely reach back occasionally and correct the wheel when necessary.
I motor into the wind at a speed just enough to make headway straight into the wind and raise the main. Once the main is raised, I bear off just enough to catch a little air, which usually has me underway in a balanced situation where I don't even have to mind the wheel. I coil the halyard and put it away. Then I ease the topping lift.
If you hank your genny, it's best to have it set up at the dock so all you have to is raise it when underway. Setting it up includes planning a side for the genny to be raised so I can pre-set the sheet on the correct side. When I raise the genny, this controls the flogging. So on a close haul, I raise the genny and use a winch normally just at the top. It really helps to have cabin top winches to go with the aft-led halyards! Sometimes I have to grab the wheel to pinch just enough to get the genny all the way up. The more breeze there is the more I need to head into wind to get it set. Then, I bear off a little so I'm motor sailing and simply coil the halyard and put her away.
Then I shut down the engine and make adjustments to sheets and traveler. There on, I'm sailing. I always sail single handed with the bungee to center the wheel. If I'm balanced well, I don't need to pay constant attention to the wheel and it gives me time to tweak adjustments. I bought a wheel pilot but haven't quite gotten around to installing it yet. We don't really have room for it, what with our constant course changes ... but I'm looking forward to installing it and enjoying all of those advantages, but I don't find it necessary for singlehanded sailing on our lake.
With confidence, you will learn what to do when the wind gets to the point where control is a real issue. I find that you have to leave yourself room, and above all be methodical. Always leave yourself with the ability to get to the helm under control with the engine running and driving forward. Keep the bow pointing up wind and manage the lines to minimize flogging without getting wind on the wrong side of the sails. If you plan the steps that work for you and keep to them methodically, while always being able to drop a line and manage the wheel, you can deal with the unexpected or difficult situation. It helps to have the halyards run through clutches and the sheets managed on cleats correctly.
It will be a while before I brave those crazy winds near Squamish to come for a visit.
