Earlier quoted context omitted.
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 so…
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.