Hi Steven,
The best way to deliver multiple files to a user when ordering 1 Product is to place all the included files in a zipped or compressed file and enter the Download URL to download the zip file. Configuring multiple Product Download URLs for 1 Product isn't currently supported but we are available to program this option. If you would like o be provided with a fixed quote to add a multiple download URL feature to the Cart, please submit a Quote Request at the following link -
http://www.smith-consulting.com/servi...
You also may be able to use the "Add Role(s) after successful payment" feature to grant your users access to a "Downloads Page" after a successful purchase.
Hope this helps!