How are people automating the data import? I can't imagine someone entering everything by hand. Lots of places don't even provide an export file you can work with... most of them offer a PDF.
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.
Most banks/CC have some sort of export - be it in CSV, OFX, Quicken, etc. Then you import it using your financial story.
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.