I haven't even started to build my boat yet, but I find myself thinking a lot about this problem: I sailed with Captain Charlie on his PocketShip a while back, and we had quite a bit of trouble getting his boat off and especially back on the trailer in a fairly brisk cross-wind. I don't see how I would do it by myself. Just so you'll know, we launched from the trailer and used a long line to pull it over to the dock, then reversed the process getting it back on the trailer--not a very elegant solution. He said later that he should have "driven" it off and on with the outboard. That would have meant that he would have used a stepladder to board and debark the boat, and I would have driven his vehicle. So I have some questions about doing this single-handed:
Are you able to climb up into the anchor well while the boat is still on the trailer and clamber back to the stern to drive it off?
When returning to shore, is it possible to reverse this process, i.e., drive the boat onto the trailer, then climb out of it somehow? (And hope it does not slide back down into the water in the meantime.)
If the answer to the above questions is no, what does one do? One idea might be to put a small stepladder by the bow when launching and climb into the anchor well that way and then back to the stern. When returning to the dock, one would put the ladder in the anchor well after backing the trailer into the water, then lower it to the ground after driving onto the trailer. Both these operations require the boat to stay in place while you are climbing in or out.
Is there a better way I haven't thought of? There is usually someone around to help, but sometimes not, or at any rate not someone you can trust for whatever reason.
Also, I want to try to use the motor as little as possible and am always trying to figure out ways to avoid it. I'm not very good at sculling, though, and even if I were I don't think it would work very well in this situation, especially with a cross-wind.