That is a very interesting viewpoint, but it makes no sense in WvW or any war, or simulation thereof.
I will say it is easier when an enemy is leading the push on a common enemy, but a truly great Server will not take the path of least resistance.
If I throw myself solo at an incoming zerg and die painfully, that makes me a "great" player? If a small group of people throw themselves at a heavily fortified tower, they deserve some consolation prize, even if they did not take the objective?
If, on the other hand, you manage to overcome a supposed "harder" target, by definition you have invested a greater amount of supply/manpower/time than the minimum required to do so, making the notion of an easy target invalid. There is no target of "least resistance", only more tactically viable targets.