Restrict access for media to a specific member

I am building a client’s SEO services eCommerce website with subscription and recurring billing using Woocommerce. My client would also like the ability to upload a report each month at the end of that month for each client so that when they login to their account they can view/download it.

So the flow is this:
– User subscribes using website via WordPress/Woocommerce.
– User purchases a monthly SEO package with recurring billing.
– Every 30 days the client logs into the backend of the website, selects a User account and uploads a PDF report specifically for each User so that when the User logs into their account on the website they can then view/download it.

* The report is only to be viewed by the User the clients specifies.