Tim
I've attached photos of lowering the rudder from the boat. If the boat is already up on land, one thing is important. You must be able to dig a hole about 12" deep in the ground under the rudder before lowering. If you can't dig, then the yard has to hold the boat up in the slings high enough for the rudder to clear the shaft out of the boat. To lower the rudder I use two 1/2 ton chain falls. I purchased them at Harbor Freight for about $30 each. Not the best quality but good enough for this job. A loop of line goes over each sheet winch and drops over the side. The chain falls are hooked to those loops and a webbing strap goes under the bottom of the rudder. The steering quadrant and the rudder packing nut are removed from inside the wheel locker. If there is an autopilot tiller arm, it must also be removed. Outside on the rudder, the gudgeon must be removed. To do that the fairing over the bronze fitting must be chipped away. The are three bronze bolts that are removed to disassemble the gudgeon. It's a good idea to replace those bolts when reassembling. Jamestown Distributers in Bristol, RI carries the right size in silicone bronze. Now comes the part about the hole. For the rudder shaft to clear the bottom of the boat when the boat is properly blocked up on land, the rudder must drop an additional foot or so below the ground. My boat yard allows me to dig as long as I replace the ground to how it was before I started.
With the chain falls in place, the rudder loose and the hole dug, it's a simple task to slowly lower the rudder by alternately lowering each chain fall until the rudder is out of the boat. So far, all this is a one person job. A second person is needed when the rudder is being raised back into the boat. That additional person is needed to guide the rudder shaft back into the boat as you raise the rudder with the chain falls.
I hope this and the photos help you with your project. If I can be of any additional assistance, let me know. In the 31 years we've owned Dana, The rudder has been out four times. With the proper setup, it's a fairly easy job.
Jim