Re: Retreiving in a crosswind
109, I agree now with you; I forgot about the dock's length. I often use a ramp that is cut into the bank so it's a different deal.
With the long docks, the side you choose is also affected by whether you have help. If you are up against the upwind/upcurrent dock and can walk it down with bow and stern lines, the problem is solved. Your second design is better for solo so you can work against the dock.
Bottom line as you said is to have experience. I suggest that it's on the bad days, and not the calm ones, if the ramp's not crowded, practice several "touch and go's."
When I was teaching my children, I'd have them touch the bow on a fixed object in the middle of the river, such as a piling, from all directions to learn how to work the wind and current. And no slamming reverse for brakes! (actually I started with a soft target like a mud bank for obvious reasons).