My rudder moved very easily when the boat wasn't moving, both in the water or on the trailer. It only started to bind up at speed when doing sharp turns. When I disconnected the tiller arm it had a very smooth action. I can't say that in my case the rudder action was any better after doing the maintenance.
Be sure to support the rudder after removing the tiller arm, or put something cushy for it to land on after it falls out. My '89 had two o-rings, if yours is similar you'll want to replace them.
I looked very carefully at my rudder last night, I could not find an external weep hole for the grease to exit.