Buford, it depends on what all you want to lube. I think it would be tricky to pull them apart with them still in place. I guess it would all depend on how much room you have under the trailer so the legs would drop all the way out. The longest piece is 33", so you'd need about that much room to take the inner leg out. The inner leg with the holes is about 24" long. Hope this helps.
I'm thinking about putting some grease zerks in mine, just haven't decided for sure and, if I do, where to put them. Those screws get a workout so some occasional grease on the threads couldn't hurt IMO.