[RussianCow]

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 granularity. When all expenses at Amazon, Walmart, etc go into the same bucket, it's really difficult to truly understand what you're spending your money on and if you have a problem you need to curb. Seeing "$X in spending at Amazon" isn't really that useful without knowing how important or frivolous any of those expenses were.

[muti]

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 against

[RussianCow]

Sure, and my Amazon example wasn't very illustrative of the kind of information that could be gleamed from tracking this at a more granular level. A more concrete example is that my wife and I were flirting with the idea of reducing our meat consumption (for non-financial reasons) and wanted to see what the financial implications would be. Another example is to try to accurately price out past trips we went on: some things normally get filtered under other categories, such as clothes or other products purchased specifically for the trip.

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.

[6510]

You can do a lot with specific and very little with generic entries.

In NL we got the banks to allow exporting [YOUR] data kicking and screaming. Nothing real time sadly but at least it's a thing now.

I would like to force merchants to do the same.

Enforce some protocol that doesn't suck and it should take 0 seconds.

Imagine the things we could build and how many people we could fire.

[xattt]

Some stores are modern-day general stores (Costco, Walmart) so you will end up purchasing from several categories on one trip (gift, groceries, home maintenance). YNAB, for example, allows for splitting a single transaction across several categories but you have to figure out what the cost of that individual item was.

It’s annoying to do in Canada where sales tax is not included. The fly in the ointment is that certain categories are tax-exempt (essential foods, kids’ clothing) but not others (prepackaged foods, adult clothing).

If your shopping trip is across three or more categories (gifts, clothing, food), you’ll have to figure out which items were tax-exempt before you can do any subdivision.

[stouset]

You don’t need that level of accuracy, you just need “close enough”. Split things out that are important, but if you’re trying to get the sales tax calculated to the cent you’re going way past a level of utility that matters. Eyeball it and move on.