Ray I tried this and it did not work. I ponied up for the latest Data Assist plugin and will post a couple shortcomings I found there in a new post.
I think the problem is that a file field creates an array of values, and parsing them to the update or insert behavior needs a proper function to pull just the [name] value and integrate this with DWs insert or update behaviors. Also appending the extension is needed if you want to save the proper name of the file being updated.