In thinking a bit more, I think the biggest pain point for me is one with plain text in general: it supports no attachments. I have my own system to refer to specific files and built a Mac app that lets me drop a file on a transaction, then it copies that file into a specific folder and adds a tag to the transaction. This could be done so much easier if the data would be sqlite, but then you obviously lose the ability to edit it directly in your text editor.

Fava and beancount have some affordances here. You can make a data directory with a directory structure that matches your chart of accounts. Place datestamped files in here and they'll show up inline in your fava ledger view.

Additionally you can annotate a transaction with a "document" tag and that document will show up directly associated in the ui.

The ui has pretty good previewing for these. I add pdf versions of all of my statements, and attach receipts to specific transactions (business expenses, proof of paying taxes, etc.)

It works quite well

You can perhaps use local file:// references in the files and open them in a browser, or you can use ledger from within a tool like Obsidian, LogSeq or DevonThink. Perhaps associate attachments in that way?

https://github.com/tgrosinger/ledger-obsidian

oh yes, absolutely! I have a system that works well for me. But it's inherent to plain text files that they don't support attachments. It's plain text, after all.

You can paste the file as a base64 string. Disable word wrap and it should only appear as one line.

A good text editor of the future should recognize these base64 strings and make them appear like clickable files, but still let you right-click and go back to the plain text representation.

ZIP can be a useful container for when you want a plaintext file with attachments, but you also want the full folder structure transportable itself as a single file. Automating zip/unzip operations isn't too bad, and you sometimes easily can teach some applications to work directly with zip container streams, without a temporary folder, too. Some existing text editors can do it naturally already; emacs and vim both have native support. Others have plugins available, like VSCode has ZipFS [1] (which is also on the backlog of possible things to support out of the box [2]).

[1] https://marketplace.visualstudio.com/items?itemName=arcanis....

[2] https://github.com/microsoft/vscode/issues/75559

+1 for ledger. It has been the best one I've used. The fact you can script it is f'ing amazing. My taxes have been on-point for 2+ years now since I started using it.

When I sold my house, the escrow company mailed me a refund check of about $3000 on the closing. I never got that check. Guess how I found out about it, 5 years later, when I started using ledger-cli?

I'm not using any of these tools yet, although this article popped up at just the right time because Quickbooks and my bank conspired to miss a bunch of transactions that I'm cleaning up now... but that's beside the point.

The strategy I've used for different accounts/categories is to make accounts that match the expense categories that the Canada Revenue Agency wants on my tax return. Early on when I was getting into it I made a bunch of accounts for logical categories (Hosting Expenses, Prototype/Manufacturing Expenses, etc) but then after a few years of trying to map those categories into CRA categories... I just realized I could pre-categorize them appropriately and make my taxes simpler at the end of the year.