I helped someone do this for their accounting job once since I saw them working with obscure data re-entry moving from old DOS systems to SAP. They had a ton of material to manually move over and it seemed painful ergonomically.

I used Sikuli from MIT to deal with the randomly changing window locations.

Management got mad at them for completing the task so quickly (it took a week instead of a few months) since it fell on management to deal with what to do with the data entries next, and they didn’t like a huge stack of work looming. Ha