Well, removed the rudder yesterday. Same thing here - with the steering cable removed, the rudder had a smooth easy motion. Removed the arm and dropped the rudder and things generally looked OK. Pretty clean and no corrosion.
Rita - where did you get the new o-rings? Mine look OK, but might as well replace them while I'm in there.
My '93 ProStar has the weep hole on the rudder box housing. I almost think that this system has to have a weep hole, otherwise you wouldn't be able to get any grease through the zerk because it would have no place to go. I can say this though - when I tried to grease it before, I didn't get any grease coming out through the weep hole. So maybe it was light on grease and this only manifested as a problem with the rudder under load?
So I'll put it back together - make sure it is greased well and we'll see how it does in the spring. If the binding is still there under load, I'll replace the steering cable.