File upload is not compatible with multiple insert / update or the manage relational table behavior.
using manage relational table, or multiple insert / update, the form element names become dynamically created, the file upload behavior will not work in this instance because it does not support dynamically naming the element name.
it will take hand coding to make this work, we can help set this up through a premiere support appointment:
http://www.webassist.com/premier_request.php