You will not be able to use the Digital File Pro upload with the repeated elements. You instead must have an upload for each file you want to upload. The names of the file fields will be whatever you have named them in the form with an _0 at the end for the first one. So if you have five file fields in a repeat selection area and the filed is named file1 the name of the fields you would need to reference in the DFP server behavior are:
This should allow you to have your multiple uploads along with the multi insert, let us know if you have any further questions.