I require a two part solution:
1) An ActiveX control that is launched from a web page. This ActiveX control will run an application that will allow the user to select a directory of files. It will identify the relevent TIF and TXT files and transfer them to a Web Service.
2) A Web Service to accept incoming TIF and TXT files from an ActiveX control. This will perform some necessary processing and insert the files into a SQL Server database.