This is more of a subscription rather than a membership.

In you mind, what are the benefits of "membership" that differentiate it from a simple subscription?

You could use Woocommerce with their Subscriptions plugin or Easy Digital Downloads with their Subscriptions add-on. Both are pretty solid choices. EDD might be a little lighter weight than Woocommerce but I think Woocommerce has more reporting details and export options for accounting software.

MemberPress, DAP, S2Member or WishlistMember