Hello Sean, We are doing something similar to this.  We have a ESRI based iOS app that allows our users to take a photo when completing an inspection on a device on the map, which is uploaded to the GIS server.  To extract these images from the SQL tables, I have a scheduled job that runs each day to extract the files from SQL and place them into a specified folder on our file server.  I then am using LF Import Agent to import these image files into the repository and finally a Work Flow to assign meta data and move to the proper folder.