As Curt mentioned, this topic has been discussed. If City Island is anything like the Boston area, you will need a couple of sticks of dynamite to dig deep enough to drop the rudder. It might be possible to hire a Travel Lift to pick up the boat.
Thank you Curt and Tom. I'm still a little confused why some could slide it in past the rudder and others couldn't. Every boat is different I guess. We do have a crane to lift with but I would have to wait for a bunch of boats to be launched in order to get to me. It will not be an easy dig so I will have to consider the lifting the engine option too. Are there any related issues dropping and reinstalling the rudder that I (hired hand) should be aware of?
Had a friend who owned a Catalina 350 (2004). I you push hard enough against the rudder, there should be enough deflection to allow the shaft to slide out. Others have also suggested removing the cutlass bearing, first, that will allow more lateral positioning of the shaft to allow it to clear the rudder. No digging involved!
i lifted the motor to get the shaft out the other way into the cabin. i do believe if i took the cutlass out, i would have been able to get it past the rudder though.. i was replacing the engine mounts anyway so did it as part of that activity.
Just read a post on the C310 Facebook page from someone in Australia who says removing the cutlass bearing makes it possible to remove the shaft without dropping the rudder. Plus you get a new cutlass bearing as part of the deal!