Your answers make me question more though.
Im glad it got you thinking!! Thats a very good quality to have in Astrology, question everything! Because there IS an answer to it.
I recently met someone who has a natal chart with Jupiter in FALL (Virgo) Essentially debilitated, with the planet slow and Retrograde, however, this planet is in the first house making a trine to Venus another ACCIDENTAL dignity. This person exhibits all of the Joyful, enthusiastic bouyant characteristics of the planet to the point that you would call them Jupeterian, or Jovial.
So in my mind at least having this accidental dignity through being in the FIRST house, many of the traits are easy to see.
The person will always be Jovial, whether dignified or debilitated. You will find however that outside (or accidental) influences will make these Jovial qualities change. The trine to Venus must be Partile in order for it to be considered an Accidental dignity (meaning not above 17').
ON the other hand though and I am agreing with here now... Jupiter in Saggittarius by being in Essential dignity and although in a weak house, (third) and conjunct the South Node, (traditional debility by accident) is broad minded, lucky, and religiously inclined. The optimism though is hidden away slightly.
Being in the 3rd House, would give these significations to the significations of the 3rd (siblings, vain dreams, short travel, writing) more than to the individuals personality (which is shown by the Ascendant/Lord & etc.). If we find that Jupiter is dignified in this position essentially, we can conclude that the siblings of the native (or their writings/dreams & etc) will be somewhat of the nature of Jupiter. This person will have a brother (most likely if testimonies agree) who is Jovial (ie. in temperament and with his significations, religious, just, & etc.). His conjunction with the South Node however declares scandals and controversies surrounding this sibling/neighbour and/or the natives writing concerning topics of religion, sciences, arts, (and other Jovial significations). At any rate, it brings scandal by way of Jovial persuits.
Essential dignity therefore comes first. But if it is hidden away in the 12th house, with no aspects? I think I might have to conclude that it is just not seen by people the way it would be done in the 1st house.
Theres a saying in Astrology "use your judgment". You are perfectly right, sometimes its accidental dignity/debility can be more open and obvious than its Essential. For each situation you should use your judgment to determine the answer to this.
One more thing... Perigrine planets are better off than planets in detriment and fall right? I read somewhere that by being peregrine, a planet loses its MODERATION, and that was the precise word used, for both peregrine and detriment and fall
Kaiousei no Senshi shares my opinion on this (and a lot of other things as well!). Each of these share different influences. A Fall indicates that one is falling from their place of power, they are descending in power and influence and therefore their influence on others is weakened. This can be seen as a leader who is losing control over his people. Hes not necessarily disposed of them, but hes certainly about to be in that position. Detriment indicates someone who has fallen into ruin. For example, a leader who has not only lost his people and influence, but also his possessions and those things which he values. He has went from a King to a Begger. This is obviously a lot worse than simply falling from a position. A peregrine Planet is like one who has no power or influence over anyone. It doesnt necessarily mean that he has falling from this position or been placed in ruin as he was never in a position of power to begin with. This would be like someone who has been a begger or wanderer all their lives, never knowing where they are going, they have no influence to command others.