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One of the mystics describes how Mary the Mother of God was calling out to Judas because she knew what he had done; but the more she cried out the faster he ran away to his tree of self-execution.

What part of the 5th Commandment did Judas not understand!

So, the Gospels also mention that Judas, when he objected to Mary Magdalene's anointing of Our Lord, wasn't actually concerned about the poor, but he had been embezzling from their common funds, so his corruption goes way back.  We don't know why.  Did he just not have faith in Our Lord or lose it along the way?  Or was he just overcome with greed? 

I still think Judas should be the focus of a series of meditations for a special "accountant's" or "bursar's" 5-day silent retreat.

I think there's a fundamental danger to being mired in worldly concerns, the bottom line. Other officials, whether at a non-profit, religious order, etc. can keep their focus on what their organization is about: spreading the Faith, teaching, forming the minds and souls of children, preaching, tending the sick, spreading the truth (news), etc.

But that poor accountant stares at a screen every day, focused on that bottom line. If only we could get more people/viewers/clicks, we'd have a higher number on that "income: donations" entry! Then the bottom line would be better.

So they will be inclined to compromise, modify their views, whatever it takes to get "more people" to support their organization (readers, viewers, benefactors, parishioners, etc.)

Just look at Bishop Fellay. He was bursar for the SSPX. It seems to have formed his thinking into a very worldly, practical, numbers-focused worldview for the SSPX. If I were to guess "what caused his fall", it's the best guess I have. Although only God knows for sure. Bishop Fellay was raised Trad; right in the environs of Econe if I recall correctly. Like across the street or something similar. So all the pieces were there, for +Fellay to become an excellent Trad Catholic.

I know the answer is "original sin" or "free will", but WHAT PART of his free will led him to his fall? It wasn't wine or women in his case. I think he just formed too human, too material, of an outlook. Probably caused by his daily work keeping the books and watching the purse and the things that were contained therein. Hey, it happened to Judas, why couldn't it happen to other religious bursars?

But I know that both Jesus Christ and Archbishop Lefebvre (who are likely in the same place right now) had bursar problems.

Some temptations are timeless. Such as a parish priest being distracted by visiting his Faithful during the week, seeking more and more human consolation (conversations, socializing, good food, "innocent" amusements, at least for a layman) instead of spending time praying, sacrificing, spreading the Faith, studying, travelling, etc.

Some temptations are tried and true go-tos for the devil, because they are fundamental to a given career or vocation. They almost go with the territory.

I agree.  Especially the neo-SSPX appear to emphasize and value an excessive fraternization with the lay faithful.  When I was at STAS, an elderly priest once visited who told us that when he was in seminary they cautioned against that.  Way too many potential drawbacks vs. possible benefits.  Faithful could lose respect for priests if they see them too often in secular settings (e.g. playing basketball, drinking alcohol in restaurants, etc.).  Also, as this priest mentioned, you could create resentment where some faithful feel the priest "favors" some more than others ... and the perception of cliques among them.  It's like if a parent favors some children the other ones are saddened and resentful of it.  Then of course there the aspects you mentioned that are more harmfult to him.  If priests get too familiar with the faithful on a natural level, it might make them more reluctant to confess sins to him, and/or they might be less likely to take his direction seriously.

IMO very little is to be gained from playing basketball with a priest or going out for drinks with him.  "Wow, that priest has a great 3-point shot.  That makes me want to be and to remain a Traditional Catholic."  Really?  "Ah, that guy is so cool, so Tradism can be cool too and doesn't have to be so irrelevant and crusty." ... Didn't they learn the lesson from the Conciliars about how this is an abject failure?