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Late post but hopefully helpful. I have a number of years experience singlehanding on SF Bay and Coastal Pacific. Where you're singlehanding makes a big difference. Most of my single handing was in a Catalina 27, have sailed Catalina 22's a fair amount, currently sailing a Hudson Force 50 (57').
I found that the many technics to tie down /remote control the tiller without using a tillerpilot (autopilot) were a big limiter to conditions that you can sail in singlehanded.
Both the C27 and the C22 are not good heaving-to boats. They can be made to heave-to but they end up broad reaching and wander more than a boat with more keel. If you're in any kind of waves/wind, the possibility of an accidental jibe is too great for a single-handed crew. I rigged my C27 with main halyard led back along with two sets of reef lines back to the cockpit. I could reef in about minute with this setup including going to the second reef in a good blow. Run lines/fittings on the main boom just aft of your reef points (jiffy reefing). I ran separate lines to forward and aft reef points because with some resistance on the sail and single line reefing system will sometimes hang up. I had rope clutchs on the cabin top for these lines although you can use cleats to save some cost. I led the jib halyard back to the cockpit as well.
While single-handing, I'm always conservative on sail area. On SF Bay (often picks up to 15-20 knots) I would seldom set out with a genoa. Usually would use a conservative jib that I didn't need to reef. As you probably know, reefing the main on a C27 or C22 makes the boat a real beauty to handle in pretty good winds.
I tried using those "convert your regular winch to a self-tailing winch" with poor results. I ended up eventually getting self-tailers for the jib winches although I sailed a lot without them as well, handling the tiller most of the time with one hand or knees while trimming with the other.
I can't say how much different you're singlehanding life will be if you have a tiller pilot (like the Raymarine ST1000). Makes all the difference in the world. You can't really depend on them to steer in any conditions requiring large deflections on with the tiller quickly, but you can easily trim up high and the have the autopilot hold you for a minute while you're reefing.
My humble opinion is that to single hand, you need to set up the boat so that you don't leave the cockpit. It's too easy on this size boat to hurt yourself on the obstacle course outside of the cockpit (and outside the boat).
Once you get the processes down that you need to use, the sailing single handed part really is a lot of fun and rewarding. One of the processes that I still scramble a lot with while single handing is setting and weighing anchor. I don't like moving fast while single handing, but a crowded anchorage kinda forces you to sprint back and forth.
Hope this helps,