Membership Subscription Page and Multiple Access Levels

Hi everyone. Trying to wrap my head around this.

I want anyone that goes to the site to be able to register (either manually or using Facebook). Once they do, they are automatically upgraded from a Visitor Status to a Free Membership.

What I would like to do is sell pages (which is still being worked out in another thread) that people will have access to forever. For example, they sign up for a free membership, purchase a course, and then have both memberships - the free one, and the membership that is specifically just for that page.

The question I am having is it seems Membership isn't allowing me to have both memberships? But instead have to keep joining them?

I would like the subscriptions page to almost act as a "My Videos" page where any course people have purchased can be accessed...

Any thoughts on this subscription page or how to achieve what I want?