Use case for membership & custompress plugins

I am about to start work on a new project for a small organisation that has a few hundred members. Some of the members pay a small amount for a short listing and full members pay more for an enhanced listing. These listings make up a directory of members that can be publicly searched based on location (they all provide basically the same service). They also get access to premium content etc. The membership plugin seems an obvious part of the solution.

For the listings I am thinking that creating a custom content type with Custompress would be the best way to create a paid for listing per user. However, is it possible to only allow each member to only be able to create one piece of content and also to restrict edit access to only their own content (ie like a profile)?