On our 23.5, I generally turn into the wind, with the motor idling in gear and the tiller tied off to keep the boat into the wind. Raise the main, then the jib. Push the tiller slightly to fall off the wind, trim the jib, then the main. put the motor in neutral, shut it off, and I'm sailing.
Dowsing, I start the motor, put it in gear at idle, turn into the wind, and tie off the tiller. After flaking out the jib halyard, I release the jib halyard and go forward to pull down the jib, bundle it up and secure it to the pulpit with a bungee cord. Then back to the cockpit and adjust the tiller if needed to stay into the wind, make sure the topping lift is fast, flake out the main halyard and release it, move to the mast to pull down the main and secure it with the stops. Back to the cockpit to untie the tiller, and I'm motoring.
It is important that you have enough maneuvering room to windward, and while you are doing all of this, you need to keep an eye out for other boats and your heading.
It is possible to run a light line from the cockpit, through the shackle at the jib tack to the head of the jib. When it's time to dowse the jib, you can pull it down using this line, without leaving the cockpit, and secure the jib when you get back to the dock.
Rob
S/V Kinship
Lorain, OH