It seems like most financial places rely on Plaid for the data integration, but that's a paid service I don't think Open-Source or free personal finance apps would use.
Chase charged like $10/mo or something like that for using OFX to download your bank statements (which is pretty ridiculous considering what it is). Eventually I abandoned it because none of the other bank accounts I needed to track offered OFX or anything similar that I could find, and just gave up.
The real pain is in the categorization (was this Groceries, Supplies, Dining, Medical Expense)?
I use KMyMoney which usually picks the same category as the last transaction from the same place. Saves some of the work, but it's still painful. I then wrote a script to export from KMyMoney to ledger format.
AI can assist, but that's it. When I go to a Kroger's store, I may buy food. Or I buy supplies. Or medicine. Or gifts. Or something else. And almost always a combination of these. We are already at 5 categories, without mentioning others. All my CC will report is a transaction at Kroger's. How is an AI supposed to guess how much I spent on each?
I (mostly) don't find it too onerous. But it is very much Inbox Zero. If you keep on top of it then it isn't much additional effort. While I'm waiting for the cashier to make change or print a receipt or while I'm walking out of the shop I can enter the transaction. But if I let a few days of them build up it becomes a more annoying 5-10 minute effort.
Also you need to do manual entry for anything you pay with cash anyway.
But the manual approach starts to fail in a family unless all involved are on-board with the data entry. (Which is almost never the case in my experience.) In practice that means all of my wife's expenses are a bit of a black hole.
I used to dread it too. But actually, in normal life, the volume of daily transactions is not that large. Besides, filling out a journal disciplines you. And VS Code does autocomplete for accounts and payees.
But. I keep my journal files in a folder and open it using the VS Code project file.
File's name is ledger.code-workspace
{ "folders": [{ "path": "/path/to/journal/directory" }] }
Yes, that's just it. I do not use anything like a language server.