I'm sorry about bringing up an old thread but I read this thread and am still stuck at what Ken said. I read a version of St. Theodora's journey and the way the account was worded, it made it seem like if a soul can't "pay up" at the toll house, the demons would take him and punish him as much as they could and through intercession prayers, repentance, etc., the soul would eventually be saved....
The problem with this is that the tollhouses are not and were never meant to be a description of reality. The vision of the tollhouses is a vision which is, in a sense, a verbal icon of the particular judgment that we all will experience when we die. It is not meant to be taken literally. If you try to interpret it literally you will end up somewhere far away from Orthodoxy (probably in Roman Catholic purgatory).
The reality is that when we die we will each face a particular (not final) judgment - the judge is God, not the demons. The demons do however attempt to accuse us before God. The subject of the judgment is our earthly life and the object of the judgment is where and how we will await the resurrection. The tollhouses are one of many attempts (however a popular and useful attempt) to explain the particulars of that reality. However, the particulars of the life beyond the grave are completely uncomprehendable to our fallen intellect and so only vague and imperfect images that we can comprehend are possible.
Of the three scenarios that you posit above, none are correct because all assume that the person is being punished. In fact it is not punishment that we talk about here, but rather the natural consequence of our own actions. If you are diabetic, is your blood sugar issue a "punishment"? If you are born blind and because of your blindness you walk into a wall and are injured - are your injuries a punishment? We are "born sinful" and thus the consequences of our sins are not punishments, but rather the natural outcome of our sins - and we experience these somehow (with some intensity not experienced in this life it would seem) in the life after death. In this life we have the chance to be cured of our infirmity - and to the extent that we are cured we escape the consequences of our illness, but not everyone is cured all the same and so some suffer more than others. This is not punishment - it is however an occasion for compassion and prayer.
Fr David Moser