Like the original customer I also couldn’t figure out how to get this to work. I’m glad you mentioned the user setting!
I’m not sure setting every customer to have purchase order access works – what happens when a customer registers for a website, wants to purchase and pay by PO? There really needs to be an option to enable it for all users by default.
If this option is only available in a premium paid-for version then so be it. As far as I can tell there are no good working PO number and PO file upload plugins in the WordPress plugins list, WooCommerce extension marketplace or on Envato apart from this one. They all only cater for PO number – not the file upload.