So, I went in head first and wrote 80% of the program before checking for existing tools... And there are some really good tools available.
This ED OCR tool monitors your screenshots folder and outputs a csv file to your documents folder. It uses Tesseract OCR and needs minimal setup and intervention. It does not contain a dictionary, so some screening might be necessary when importing data.
I hope you guys find this useful. critic's ED OCR
This was a quick 2 day project, I would suggest using it as an alternative to some of the other well maintained tools. When needed I will make the source code available.