Your rudder won't fall off unless you unbolt the pintle. The stuffing box at the rudder shaft relies on a compression of packing flax (
http://www.westmarine.com/webapp/wcs/st ... vPY8_ltxpw ) by a collar that bolts to a fitting that is attached to the shaft log/tube. This is very similar to the drive shaft stuffing box from the engine set up. It is also above the static waterline on our boats, by about a foot. I don't remember the thickness of the flax packing but I would guess it's either 1/4" or 5/16". You will need to remove the quadrant to access this area and while you're at it, you should inspect the steering cables closely for frayed strands. Of course you will need to unbolt the compression collar, remove the old stuffing flax clean off the rudder post, install new flax, re-bolt compression collar to snug but overly tight. re-install quadrant. By the way, mark your steering cables for placement before disassembly so you can reinstall the same way.
Not sure if I explained it all clearly but once you start digging into this project it all will be very clear once you remove the quadrant.