My wife is non-technical and doesn't know anything about bookkeeping. Every-ish day I ask her for receipts and enter them into our ledger-cli file. She mostly uses her debit card, so it's usually easy not to miss too much. (I use cash exclusively, so it's more of a conscious effort for me.) Every month I send her a monthly report via email.
I created a little app that tracks the cash spending that I can export with a CSV file. You can host it yourself. I had no idea that my wife was using so much cash!
