What I do....
I deal with this a lot as I keep the rudder up and out of the water when the boat is in the slip and because the channel is very shallow in some areas I tie off the rudder at a 40 degree angle until I clear into deeper water.I stand on the back transom (H240) and give the rudder a little push to get it started and then pull on the downhaul line to bring the rudder into the positon I want. I also tie off the downhaul line to the cleat to secure it in place. I have tried the wingbolt to hold the rudder in place instead of tieing off the line, but under sail, the wingbolt fails to hold the rudder down and the rudder floats up to the surface. I have even tried using a wrench to secure donw the a bolt but then the rudder does not move at all and as I said, I need to bring it up to 45 degrees when I enter the channel.Overall it works very well and I feel fortunate having the hunter as many of the other boats with fixed keels or fixed rudders can not make it out of the channel or get stuck.Backing up with the rudder in the 45 degree position or even higher, maybe tough on the equipment, but when I stear, I use the rudder and the engine in combination. I am able to reach the engine handle while sitting on the starboard and I do have remote controls for the engine.More than you wanted to hear but I hope it may help.Daniel