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Lazy jacks or a topping lift will let you set or drop your sail without being perfectly nose to the wind.
Setting sail is easy enough to do under power, but dropping the sail can be easier if you have both hands. I've found that running the motor is just one more thing to have to worry with. Adrift with the centerboard all the way down I find my boats will keep themselves close enough to the wind, particularly the Picnic Cat when I have my weight up by the mast. Either boat, I just leave the rudder free when I go forward and it works out OK. Seems like it wouldn't, but the boats sometimes (sometimes?) handle themselves better than I can.
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