OR Version 2.5.8

Similar to the "Featured Listing," or "User Action" Yes/No option, I would like to make "Uploads/Images" and "Uploads/Files" an on and off (Yes/No) options for my free listing customers.

Additional, I would like login as admin and populate my datebase by adding free customers listtings with the same email address or without an email address at all.

Any assistance will be greatly appreciated.