Take a look at http://member.wishlistproducts.com/. This allows you to have different areas/content for different levels of members (like my Academy). I’m not sure this quite fits what you are trying to achieve and how you could use it with listings – but it may fit for you.
It sounds like you have a complex project. There may be a better (different approach) you could take. If you are happy to share the brief I give you my thoughts on alternative approaches that might still fit the business requirements.