I don't think it's entirely difficult to judge ones situation once they get to D.III and field a competitive team to the point where they can evade the relegation series.
Depends on the III. In III.5, for example, a team that is currently ranked in the top 250 in the USA is guaranteed to demote because one division has a bot and a team ranked #570 in the USA, and the other division has a team ranked #378 and one ranked #248, and then the other 12 teams are all in the top 200 in the USA.