Earlier quoted context omitted.
I did this exercise for a little over a year to understand my expenses in detail. Like the OP, I found it really frustrating to do with any bookkeeping software I tried, to the point where I eventually gave up as I didn't think it was worth the effort. I started writing a web app to make this easier but just didn't have the motivation to finish. With that said, I learned quite a bit as a result of that level of granu…
There are many levels in between tracking at the "Amazon" level vs the "Meat:Pork" level. For example I currently track all unprepared food shopping as "Groceries", and would break down "Amazon" shopping into categories such as "Electronics" or "Books". Ultimately it comes down to how much effort you want to spend categorising spending, but there are many levels of granularity and orthogonal dimensions to slice again…
This level of granularity probably isn't worth it to most people, but I found it useful as an exercise to do once because it opened my eyes to insights about my expenses I never would have thought about otherwise. And if there were software that made this super easy to do (<1 minute per entry), I might still be doing it.