Opt-in is a decent enough method. But "Occasionally re-prompt a user" is a horrible idea, in my opinion. From a user perspective, that's kind of like the software forgetting the options you set. The very first time that something re-prompted me about something I had already opted-in to or out of, I would feel intense rage that it's asking me something that it had already asked me.

You would feel intense rage? Jesus. That sounds like intense overkill. You might be quite unlike an average person if you specifically--and without fail--recall every choice you've made forever when you're in the process of setting up tools.

No, it's not at all like the software forgetting the options you've set. It's the software, in the interest of providing a user with the greatest possible control over their software, while having the average user's propensity to forget minor details in mind, offering the explicit option to re-evaluate a prior choice in the future without having to remember to do so, or manually recall the way to do it.

Moreover, when I threw out the off-the-cuff idea to occasionally re-prompt, I set that occasion as an annual one. You're making it sound in this overreaction as if I suggested it to occur every few days or weeks. Instead of instantly going to such unwarranted extremes as full-on-intense-rage-mode-11, thinking to yourself, "Oh my fucking god, what the fuck is wrong with this developer that s/he'd dare to ask me this question I answered 2 years ago again?!", you might pause just a moment to consider it to be a little like recalibrating a tool that's been in use for some time. Few people keep static positions on things. Such recalibration doesn't need to occur at every minor upgrade, but perhaps major upgrades might want to ask the user to review their settings/choices.

I've changed my position on things I've opted in/out of at various times. When it's privacy-related, I've increasingly developed a harder default stance over the last 15 years. I wouldn't mind if my tools asked me to annually review old choices I've long forgotten--much like I've heard Facebook offers people their little privacy checkups (ignoring for the moment the efficacy of such a checkup when everything you do is tracked). Many people other than me reacted to the way in which the analytics "feature" was included in homebrew with surprise, because many of us never noticed the notification, and a great many of us believe tracking is something that should always be opt-in, not opt-out. However, as of this writing, I can't recall exactly what my current homebrew setting for analytics is, and I can't recall how long it's been since I last checked it to ensure it is what I think it is.

But hey, that's just me, friend. I can't remember every choice I made last month, much less last year, two years ago, or any time before that. If you do, that's cool. If you were using a tool I created/maintained, and I wanted to cover all my bases, I'd simply give you a way to say, "Don't ever fucking ask me this question again or I'll rage tweet what a forgetful little shit you are." :)

I stand by my intense rage that I would feel if some software I was using asked me a setting question that I had already set (for no reason other than the length of time since I last answered the question). Sorry, but I'm particular about my user experience. I'm not arguing anything for or against the privacy concerns, as I do not believe the fact that this is a privacy setting means it should be treated differently than other settings.

I guess I should have gone into specifics about why I don't like that idea... I can think of lots of things that let you set a setting and say "never ask me again", but those aren't quite the same. They're usually for things that get asked _every_ time you run those programs, so until you select "never ask me again" you're not actually setting the setting, you're just giving a temporary answer for that one use. Notice how this differs from what you've suggested (asking you based on an arbitrary time period). Your suggestion is a different paradigm than the already existing ones. I can see a case for having it ask you if you want to be tracked each time you run homebrew, or each time you upgrade homebrew, but doing so based on an arbitrary time-based interval (be it days, months, or years) seems odd and needlessly different than the existing accepted UI paradigms.

Oh, and I'm not sure Facebook's privacy check-ups is the best analogy. I always thought they did the check-ups when they've specifically changed something and need to give you the option to opt-out of the change, not as a friendly "do you still want your settings this way". Maybe I'm wrong about that, but that's what it always felt like to me when I was using facebook more, since I'd see a lot of articles/blog posts about new changes, and then the next time I logged in I'd get the privacy check-up.