I never leave the dock alone. The problem is that I just can't predict what conditions will be when I return. The wind can be on the nose, to port, to starboard, or behind me. Currents run parallel with my slip. The exit to the marina is to the left in the pic below.
Here is my situation;
I'm in the slip occupied by the boat in yellow. You can see that the fairway is tight, and there is usually a SeaRay 340 in the slip next to me...
My boat is 35' long, and I believe that the distance from the piling to the end of the slip is about 33'.
Here is another view;
What I do when leaving is; Double the green line on the bow. Start the motor, cast off all lines except the green bow line, put the boat into reverse. Because prop walk will push my bow to starboard, I do not let the crew on the bow release the green line until the bow swings to port (or is next to the finger pier). I even encourage them to give a tug on the line to help pivot the bow to starboard.
If the crew on the bow releases the line early, and the bow does not swing to port, I will back down the fairwary.
I have fenders out, and bow, stern and spring lines rigged before I enter the fairway. When I enter the fairway, I have crew go up to the shrouds (the red arrow), with the spring line (red) in hand, and prepare to step onto the dock. As soon as they can, I have them step onto the dock, and secure the spring line first. I then put the boat into reverse to stop any forward momentum, and prop walk pushes the stern to snuggle against the dock. I then tell them to QUICKLY go forward, and grab the port bow line (green) to keep me from swinging into my neighbor's SeaRay. As they do this, I step off and secure the stern line.
I am open to suggestions, but I can't imagine doing this single handed.