You could make it opt-in telemetry in the tool itself, that would probably be good enough.

But also, you could probably be just as accurate by asking an LLM to order the options by popularity based on their best guess based on all the tutorials they've trained on.

Or just scrape Stack Overflow for every instance of a command-line invocation for each tool and count how many times each option is used.

Ranking options by usage is the least complicated part of this, I think. (And it only matters for the popular options anyways -- below a certain threshold they can just be alphabetical.)

> But also, you could probably be just as accurate by asking an LLM to order the options by popularity based on their best guess based on all the tutorials they've trained on.

> Or just scrape Stack Overflow for every instance of a command-line invocation for each tool and count how many times each option is used.

Even trusting the developer's intuition is better than nothing, at least if you make sure the developer is prompted to think about it. (For major projects, devs might also be aware that certain features are associated with a large fraction of issue reports, for example.)