In Met. Macarius' of Moscow chapter on this in his Orthodox Dogmatic Theology, he presents all the Scriptural and Patristic evidence, answer some questions, and is able to explain the question of Toll-houses. It seems that his explanation does a lot more in furthering belief than Fr. Seraphim's (though I like the departed Fr. Seraphim's writings) sometime confusing writings.
Jonathan's reference to Fr. Steven's writings provides good information. There are the two homilies by St. Mark of Ephesus on this, as well as the 18th (?) Decree by the Synod of Jerusalem (though, this decree in its final published form that we have, was a little modified to remove things that were seen to be Roman Catholic distinctives, while the substance was preserved).
I suppose this can seem jaring, and is to many. Many might wonder, "So, if I don't bring forth works worthy of repentance and/or don't pass through all the toll-houses, I'll be consigned to Hades until the prayers of the Church beseeching the Divine Compassion are able to liberate me to Paradise? This seems frightening! Why could this not even happen to the Rich Man!?"
First, the Rich Man did not die with repentance but having not brought works fruits of repentance (which St. Mark and other define as fastings, vigils, alms, etc). He died in his sinfulness with no repentance. Secondly, it seems even in the Rich Man's case he still was behaving like he was somehow in charge, even asking Abraham to order Lazarus to be the messenger. Third, his concern was also with the pain there, which is legitimate, but, he seemed little or no concerned with the attitude that brought him there, and his separation from God. True, the Rich Man was concerned for his brethren, which is why he wanted Lazarus to help, but, that seemed to be something that wasn't seen in his favour by the Lord.
I'm sure everyone here has heard the old Russian story of the woman in hell and the onion.
In the early Church for some centuries, Confession was not private as we see today. There was a public function to it, either the class of Penitents made their confession to the Bishop, or to an appointed representative. They were then given all those long penances we see in the Pedalion. They were expected to fulfill them, and to stand in the Narthex, and in some places and cases, they were expected to stand outside the Narthex in the Penitents Porch, kneeling and begging the prayers of those entering. After their penance was completed, they would be re-admitted from their time of excommunication, and the Prayer of Absolution was then read over them by the Bishop or the Presbyter appointed so to do. Needless to say, this experience, if embraced piously and sincerely, was, very humbling and humiliating (since we need humility to drive off pride!), and was carthartic in its effects. This old penitential system, combined with the period in which the Church lived for a few centuries (under persecution) was enough, by God's Grace, to offer to anyone who followed such to be in a much different state than we are today.
However, this system, especially after the end of Persecution and the opening up of the Church to a "wider audience" led to many scandles. The historian Socrates recounts a period in Constantinople in which they seemed to be in a transition phase between Public/Private Confession. A woman confessed to having committed adultery with a deacon, and confessed it to a priest. The matter became open knowledge. There was a great scandal. Pat. Nektarius decreed that there would be no more confession in the city. It was not a very good time. However, the solution was eventually given (by monastic influence) by the introduction of private confession, ostensibly, with the Priest having the obligation to keep secrecy. While we may like Private Confession a lot better, since, we are only humbled and humiliated before our spiritual father, we do necessarily endure all that was once entailed and endured. One need only read St. Ambrose' work on this matter "De Penitentia" to understand this.
Confessor today more often then not avoid giving many of the 'harsh' Penances found in exomological manuals (unless, of course, you are dealing with subjects like murder, etc, or subjects of out and open public knowledge).
Let us ask ourselves if after we repent, go to confession and receive forgiveness, do we really show forth fruits of repentance in our life. Most of us probably can think of times in which we don't, or later forget about the whole situation and seem to move on without regard for the scars, though the wound is healed, the mark seems to be there, though it fades with time.
The concept of the 'time' we might spend in Hades seems frightening, but, only we don't realize that we have the sure hope of deliverance by God's Mercy. They are sometimes call the Prison-houses of hell (at least in some catechisms). We don't have to undergo tormenting of purgatorial fire and until our temporal guilt is fulfilled and/or the treasure of merits is given in aiding us. We do find more and more relief from the things done for the departed, the Liturgies for the dead, memorial services, prayers, good works, lighting candles, etc, etc.
At the risk of undoing some of what was said above, it must always be kept in mind that such things seen in the world beyond the grave are ultimately expressed to us in symbols, metaphors, analogies, figures, though they are real. We can read the Martyrdom of St. Perpetua and see an example of someone being moved from Hades into Paradise (though the case mentioned there is even more extreme in circumstances and persons than those mentioned above).
All the things above were terribly disconcerting to me, or perplexing I should say, when I first was taught them and then read the sources. It is one things to hear some dryly state that "this is Roman Catholic teaching!", but, it is quite another to explain why no Orthodox thought so for all these centuries.
In Christ,
Fr. Enoch