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There are few things so valuable as a good user who is willing to work with you. Many years ago I worked at a company that was going to shutdown a very buggy product. There was one user who relied on it heavily and convinced the CEO to make one more release, and I was tasked with working with that customer to make it happen. Over the next month, we fixed the bugs (I coded, he tested). We wound up making a stable and more user-friendly product. It was a real pleasure to work with that guy. The company still mothballs the thing, but I know we had at least one happy customer in the end.

A variant of the first is the highly imaginative user who keeps coming up with new variations or expansions of their idea. It’s not malicious but it can be exhausting.

Especially if you try to address their core need but their imagination doesn’t extend quite far enough to see how your effort would help, because they love their ideas.

I can imagine the kind of person you're describing, and I find the idea of the burn they get from reading this hilarious. They sound innocent and quirky.

I would describe those as a variant of the second, not the first. Those imaginative users may be polite, but they’re not understanding. While not rude, they are their own brand of entitled and high maintenance (I like your description of “exhausting”). One major reason I put them in the second category instead of the first is that the result is the same from my side, i.e. I interact with them as little as a I can.

To the first kind, in contrast, I’m happy to answer any question, no matter how silly it may seem, because I can be confident they’ll trust my judgement, that they’ll learn from the interaction, and that the next one will be even better. Just about the only thing I’m sad about regarding those users is that as they grow they start interacting less because they don’t need it as much, as they are able to help themselves.

Now that I think about it, that seems like a good way to differentiate: The good users delight you and demand of you less and less; the bad users drain you and demand of you more and more.

Fortunately there's significant correlation between quality of communication and quality of ideas, so your approach might just be optimal!

> [...] I decide to take the time to explain [...]

Do you just explain or do you start by asking a question?

What I usually go with is _asking_ what they want to achieve. Because usually, the user describes features/functions/forms instead of explaining the business case. And while the user describes a business case (a thing that generates him money/...) it becomes obvious how/why to implement the request.

So often, people forget to just ask and listen.

Due to the XY problem what they ask for often isn’t what they need. And what they yell about won’t make them happy.

By and large I’ve gotten better feature requests out of looking at patterns of frequently asked questions and turning them into tasks instead of reacting to negative feedback.

> In contrast, if a user has been rude, entitled, and high maintenance, I may end up not even trying to reply in the first place because I know they’ll just be combative every step of the way,

get paid. Stop this nonsense. You shouldn't work for free it makes you disagreeable (I am the living proof).

> I guess the moral of the story is don’t be a prick to the people you’re asking something from.

This is your salary. That's how you get paid. In power. Power over what? "I am a latex maintainer". I'm not impressed. You're wasting your time. Show me your Ferrari instead.