A co-worker in a different program whose invoicing was much simpler and more straight-forward tried to automate this using OCR and Python and had a higher error rate and still had to set hand-written checks aside to handle manually.

I couldn't find an OCR system which was:

- free/affordable

- able to cope with arbitrary check sizes/hand-written checks and my occasional need to arrange multiple invoices in a stack with the check rotate 90 degrees so that all the numbers are visible

- which would capture the data from a scan in such a way that it could be easily used to rename the file

If you know of a system which is flexible enough to do this which is essentially free, let me know.