Fr. Seraphim (Rose) and all of the saints and Fathers who spoke about of the passage of the soul from the body and the trial which follows, state very clearly that the image of "toll-house" is a rather crude and earthly term used to refer to spiritual and bodiless realities. The fairly common use of the term "toll-house" in patristic, writings (as well as in hymnography, hagiography, etc.) indicates that this image was something very meaningful and significant to the saints and fathers, that it was a particularly appropriate term for describing this reality. However, the term "toll-house" seems not to have the same meaning and significance in most of contemporary society, and often results in unnecessary confusion and misunderstanding.
The demons do attempt to hinder the soul from its ascent after the separation of the soul from the body (though there are no physical/material "booths" and no exchange of money). If a man did not adequately confess his sins, repent, depart from evil and do good during his time on earth there may still be hope for that soul's salvation but only through the prayers of the Church and the giving of alms on behalf of the departed. Commemoration of the departed, especially during the first 40 days after a man's repose, is of particular importance in this regard. In the end, however, the ultimate fate of each person, and the final result of the prayers offered on behalf of the departed, is usually known only to God and is hidden from those on earth. Consequently, we must do all that we can to prepare so that we ourselves will be blameless before God at the time of our repose, whenever that might occur; and also we must do all that we can on behalf of the departed that they might find mercy before God at the Last Day.