It's about the value to you versus the effort you put in. For me the granularity you are talking about is too much effort. All my supermarket shops go in one big category "groceries and household".
Start easy and see what you want to get out of the data. If you can store the original source (e.g receipts) so that you can later go back and increase the granularity if you find yourself wanting it, that would be ideal.
I don't get all of the complaints about the tone of AI chatbots. Honestly I don't care all that much if it's bubbly, professional, jokey, cutesey, sycophantic, maniacal, full of emojis. It's just a tool, the output primarily just has to be functionally useful.
I'm not saying nice user interface design isn't important, but at this point with the technology it just seems less important than discussions about the actual task-solving capabilities of these new releases.
You can't extrapolate from your own experience in that way. There are billions of people having a different experience to you in a multitude of different ways.
Then just don't go? I personally prefer mixed gender spaces but I can understand why some people might prefer single gender spaces. It doesn't mean they necessarily have "an issue".
The diff will tell you what's changed, but it doesn't tell you the "why" of the change. A project should store that information somewhere; whether it's in pull request descriptions, issues/tickets, or the commit message, which is a perfectly reasonable choice.
Start easy and see what you want to get out of the data. If you can store the original source (e.g receipts) so that you can later go back and increase the granularity if you find yourself wanting it, that would be ideal.