I have ordered a new top and bottom rudder plate assembly for my S22.  Thanks Capt Rick for not letting me order two of them and the basic directions below.  I didn't find any step by step directions so pls. give me any advice... 
Changing the Rudder / Rudder Assembly
The rudder port is complete: The top piece and bottom.  MSP0010173 RudderPort,w/BackingPlate,Bronze 17  17  $89.47  $25.00  
 
-Remove egrease fitting 
-Remove 4 nuts inside boat 
-Remove tiller arm nut then bolt
-Do this on trailer and put boat in water allow rudder to drop out...
I have a couple of conerns here...
The last bullet and if I will need to "caulk" or put any sealant between the plates on the outer hull.  
I noticed after hitting the log that there was a white sealant showing when looking at the bottom rudder plate.   And I'm fine with basic screwing and unscrewing / adjusting.  But I would rather not drive away from my tools near the water to loose my rudder.... hence why I don't want to be far from my tools.  This will limit multiple trips.  
Any advice greatly appreciated!!
Brian
PS I would rather loose my boat mechanic virginity on something above the hull!