I worked somewhere that did something similar. Their product would scan and extract data from documents. Even working with the banks and companies who produced the documents, there were very stringent requirements (like identifying marks on pages to tell what document type we are looking at, pages being fed in the correct order, etc). Plus the ability to handle degraded, damaged, or bad copies. It's apparently one of those things that seems easy at a glance but the edge cases end up employing a whole department (they had people to review the scans and press OK or correct the data). It was a legacy system and I think a newer rewrite could get further but I'm wary about saying it could be fully automated.

90% automated is sometimes 90% as good as fully automated. It's not always the case, there are cases where hitting that 100% enables you to do things that were just not possible at all before, but sometimes it is. Recognizing those cases where a 90% solution is a 90% improvement at a 10% cost is a valuable skill.

Yes it's also part of the reason I prefer coding for myself. I can ignore a lot of "what ifs" and edge cases because I'm always there to pick up the mess if something happens. I get to focus on the stuff that makes an impact and forget the idiot-proofing :)

Or said another way, it can be fun and also effective to "Do Things That Don't Scale" [http://paulgraham.com/ds.html].

There are commercial OCR software packages that can do it. FineReader is one example (and it's been around for ages).

FineReader seems like it would have done the job.