A political candidate?

Yeah.

What might a newbie candidate...want a private investigator to look into?

These are categories rather than specific ideas, but here is what came to mind:

Political

• opposition research
• own party research
• vetting campaign donors
• vetting staff
• extortion/blackmail/threats
• scandal claims

Personal

• vetting family
• vetting alleged family
• vetting significant others
• extortion/blackmail/threats

Which would fit your story? Which allows for the most mis-leads and twists?

a lot of choices here, especially for people who knew each other previously...thanks, Dan.

This PDF document by Javier Grillo-Marxuach on screenplays is AMAZING.

OK, I'm only 10 pages in, but, yeah, it is!

Is it weird that I feel like I might be able to apply some of this to constructing emails?

A resignation letter:

Here's the thing, you see: I'm a hobbyist. This is what I do for fun.

Yes, I've been administering mail on Linux and Unix systems since about 1994. But they were my systems; I didn't need to answer to anyone but myself. I have done similar things for ASI/BayCon with a bewildering array of email systems, all of them on underpowered hosts with unconventional interfaces: I make sure the email gets from point A (usually outside) to point B (usually a set of staff members.) Like racing tiny sewing-machine-motor go-karts, the constrained environment is part of the fun; doing more with less is a chance to develop and enhance a certain set of skills. I have never had to deal with retention policies, administrative lock-outs, massive email abuse, or any of the thousand other insults that corporate email administrators cope with every single day; those are not in the skill-set I have chosen to develop.

There's a reason I didn't choose IT as a profession. I'm a mathematician by training, an early user of social media by happy accident, a science fiction fan by some force related to but quite unlike peer pressure, a writer of prototypes in both code and prose by temperament, and lately, a manager of engineers by slow evolution. None of these aspects of me are particularly well-known for compliance or even acquiescence.

When I look at the future of ASI, on its evolutionary journey from "five sci-fi fans in a trenchcoat cosplaying as a corporation" to a real, serious 501c(3) tax-exempt non-profit comparable to SFSFC or AAE/FurCon, I do see places where I might be able to help. But I volunteered to do non-profit systems management for the STOP AIDS Project in San Francisco twenty-plus years ago, and it looks nothing like what I do for fun. Handling email that might have indications of someone's HIV status in the days before widely-accessible treatments gives a whole new meaning to "are you sure we need to hang on to that?" And it was in that spirit that I made my promise to [Registration Head] and [Registration Second] that we would use people's freely-volunteered health data [proof of vaccination, required to receive a badge for this year's con] wisely and discreetly, and that we would get rid of it the first moment we reasonably could.

Being told by ASI's Compliance Officer that "the first moment we reasonably could" is in fact two years from now rather than the day after con was, to put it very mildly, a shock. Being told that after the data had been collected, rather than, say, when the possibility of it being collected was being discussed on this very list, was rather more than a shock. "If you collect this from people, we're going to have to hang on to it for two years to comply with our data-retention policy" would have been a great thing to know before I pushed the button to create the list. But that button cannot be un-pushed, just as the data cannot be un-collected.

So, [Head of Registration], would you be so good as to convey my apology to [his Second, who is not on this mailing list]? Because I do feel that I have broken the spirit of my promise to you both, if not the letter. My word means a great deal to me, and I don't break it lightly, even when there are changes to external circumstances.

And having done that, and apologized for it, I find that I need to step away from my hobby for at least a little while. Just as one does not expect a tiny sewing-machine-motor go-kart to carry two years' worth of spare tires and lug nuts, the current mail system will need to be replaced by one that has provisions for rolling retention windows and other corporate necessities. I have no interest in (and no aptitude for) driving an SUV of an email system; that is best left to those with both the training and the inclination. But I hear that ASI's Compliance Officer is working for a company that specializes in training people to do such things; perhaps his company might train the next Postmaster, at ASI's expense?

Nice, Karl. Very clear.

the current mail system will need to be replaced by one that has provisions for rolling retention windows and other corporate necessities.

Translation: "You are going to have to spend some resources. Time, money, energy. Remember the saying 'Good, fast, cheap: pick any two.'"

Thanks, dcp. Got feedback from some folks I sent this out to for beta, and the consensus seems to be, "Very nicely written, but no one on the Board is going to care about either the vaccine card retention or the creeping autoritarianism inherent in one person calling himself the Compliance Oficer and then ordering us all around like we're a bunch of minions. Yeah, corporate compliance is a pain, but we have to do it and he's the only one among us who knows how."

Hope everyone else is having a better Friday than I am.

Even so, having your letter lay it out for them might lead someone who doesn’t presently care to eventually do something.