According to what I have read, there are precedents to the kind of epic journey you have in mind. Some years ago there was some organization that offered trophies or some kinds of awards to cylists who cycled the perimeter of the contiguous United States. It was through or because of this organization that I began reading about various feats of cycling. If you google "perimeter club" or " perimeter cycling club" they might still have information on it. Some people have made a point of cycling the perimeters of so many states, and through so many states, and the perimeters of countries.
The perimeter club, or whatever it was called, wanted journals and news articles to verify the trip, and they thought the entire trip should have been completed all in one trip. That last requirement in my opinion was not very fair because it limited the awards not necessarily to good, enthusiastic cyclist tourers, but to those who could afford to take off eight or nine moinths to do it. I think they said they were willing to consider those who had proof of cycling the perimeter of the lower 48 in stages as long as they had serious proof of having done it.
I do not know of anyone personally who has cycled all the states, but I am sure I have read stories of those who have, and all fifty too.
