Re: Singlehanding- Flaking the Main
You don't need an autopilot. Just steer into the wind and lock off the rudder (using the brake on a wheel system, tiller tamer or line cleating the tiller in place on a tiller boat). An autopilot hooked into a wind system is helpful if you are sailing in gusty conditions.
Dropping and flaking on a ~30' boat only takes a minute, I do prefer to do it on the water and find that it is safer to do this instead of having sail fabric everywhere when I'm trying to dock. I may reflake at the dock if I had to rush the job, but it can be pretty annoying if the flakes aren't right so I try to just do it properly the first time.
I don't have lazy jacks. I've had limited experience with them, but mostly found them annoying.
boats that I sail on regularly: Pearson 28-2, Rondar 505, Yankee 30, Blanchard Junior