I read that the reason Christ is shown taking the soul of the Virgin, in the icon of the Dormition, is that she was terrified of the demons of the toll houses. It says that she begged Christ to personally escort her soul through the toll houses because she was afraid she might not make it. If the Holy Virgin had to be afraid that she might not make it through the toll houses, then there is not hope at all for the rest of us and we might as well just give up now. Also, if the Virgin was terrified of the demons, then why do we bother to pray to her to helps us against them?
Point well stated. I have heard many such questions over the past several years. Let me first indicate where this story about the Dormition came from. There is a Gnostic document called "The Bandlet of Righteousness." It is also often called "An Ethiopic Book of the Dead." This story about the Virgin fearing the demons and the toll houses come from that book. In this Gnostic document, the Virgin is given the "secret names" of Christ. She can pass the demons by saying one of the secret names of Christ. Most of the text of this document is taken up with endless "secret names of Christ," all of which are worshipped (like the "Holy Name" heresy on Mt Athos in the 19th Century), and all can help get one past the "aerial toll houses." This is classic Gnostic spiritual cosmology, and is all so common among reilgions emanating from ancient Chaldea and Egypt. Indeed, the entire myth of the Aerial Toll Houses comes from the Gnostic/pagan sources. Many of these Gnostic writings and other pseudo-epigraphica were taken seriously by elements in Russia. For example, the tale of "The Descent of the Virgin Mary into Hell," which is simply a re-write of the Babylonian myth of the descent of the goddess Iannana into Hell, was often quoted in Russia.
..Hopefully, all Christian people will eventually learn to disregard these Gnostic/pagan fables and turn to the Holy Scripture as the touchstone of faith. Put the notion of these imaginary aerial toll house and demonic judgments out of your mind completely. Such stories can only be propagated by a diseased mind, and one that assimilated little from the Gospels and the holy fathers.