This is a good nudge to choose the grammatically correct option, thank you.

I originally had "less meetings" before an LLM corrected me into using "fewer meetings". Then when talking about Orgtools to a couple people I heard them say "less meetings" and switched back thinking that sounds slightly more natural (but incorrect).

The way I think of it is "few" if they can be counted, otherwise, "less"

That's not really true, at least, outside of prescriptivist linguistics.

> Less has been used to modify plural nouns since the days of King Alfred

https://www.merriam-webster.com/dictionary/less

More reading on Wikipedia: https://en.wikipedia.org/wiki/Fewer_versus_less