You cant over grease them. They may have been to tight or too loose. The Dexter instructions say tighten to 50 ft lb while rotating then stop turning, loosen nut, then finger tighten until snug and install pin or back off to line up with next hole. Do not go past finger snug. When you do this and you have to back up to the next hole you can end up with them just a little loose and the tire wheel assembly will rock ever so slightly.
You dont want them pre loaded to get the pin in. Dexter is saying run them slightly loose rather than loaded. I ran into this on 2 of my hubs and shimmed them. I wont run wobbling tapered bearings and have never found any other manufacturer or application who would run a tapered bearing loose. Many applications such as ring and pinions actually preload them X amount.
They could improve on this if they used the sheet metal nut style adjuster with more slots which fits over the nut. It gives more adjustment.
Finer threads give more adjustment to any mechanism. With these axle nut set ups, depending where the hole is drilled and where the slot of that particular nut on that particular axle all fall, You can be very close to having the pin go in when finger tight, yet when you back off to the next slot you will feel the looseness when assembled with wheel on.
Use high quality grease and be meticulously clean when greasing. Use brake clean and air pressure on the parts and in do it when no dust and trash are blowing around. I have put almost 20,000 on mine. I touch the hubs and the tires often and both are warm not hot.