I single-hand most of the time.
I own a C250 centerboard model. Like Gary says, the C250's board weighs less than 100 pounds. The C25's swing keel weighs more like 1500 pounds and requires a winch to raise and lower it. The C250 doesn't require a keel winch.Nine times out of ten, I am singlehanding my C250. Leaving the dock under power doesn't present any problems. I lower the centerboard on the way out of the marina. Raising the main is easy enough because the main's halyard is run to the cockpit. I usually stand in the companionway and raise it by hand; the winch is not needed. I keep the motor running in gear at just a bit above idle to keep me pointed into the wind while the main goes up.Once the main is raised, I kill the outboard and raise it out of the water. While steering from in front of the wheel steering pedestal, I unfurl the jib. While underway (sailing), I usually sit on the coaming abeam the steering pedestal. Since I went to a 30" wheel, if I sit in the cockpit, I usually sit in front of the wheel. You need to be able to quickly access the cabintop winches during a tack or just to trim the jib. I sit behind the wheel only on long downwind runs or while under power.Furling the jib and lowering the main is just as easy. Reefing in heavy wind may be the only difficulty. Make sure you reef early if the wind is expected to build.I motor back into my slip without worry. Rotating the outboard in addition to using the rudder will allow you to make much tighter turns. My slip is only 10' wide. My boat is 8.5' wide. Not much room to miss in a crossing wind. The only time I'm worried is when I have a strong following wind and have to turn into the slip. There is only about 30 feet between my dock and the adjoining dock . . . so the turn has to be quick and accurate. Larger boats with inboards can turn on a dime. Our smaller "stern driven" boats are less nimble in tight spots.