Hi Chip,
Apologies for the delayed input...
If you have an actual grease 'cup' still in place, you may want to consider removing it and replacing the cup with a Zerk fitting. The cup can be un-threaded from the rudder post tube, and the Zerk fitting can be threaded in... it is that easy if you get the correct size Zerk.
When I did this years ago I bought the Zerk fitting at NAPA Auto Parts... was very inexpensive - a few $'s for a pack of 4 or 5... only needed 1, but they didn't have single pieces at the time.
With the Zerk it is much easier to get grease (using a grease gun) to the rudder post, than filling and turning a grease cup. You know you have a sufficent amount of grease surrounding the rudder post when is begins to appear at the top of the rudder post housing. Move the rudder back and forth (stop to stop) while injecting the grease to ensure even distribution.
If you search for Zerk Fitting in the discussion group you may find some additional information/photos to help guide you.
Peter Grabow
S/V CAKE WALK III
1987 30U 430
Stamford, CT