Create a directory with WP Types, Views, CRED (Toolset) that has the following functionality:
User becomes a member to submit a free listing or a premium listing. They can submit more than one of each. Payment goes through Paypal. After submitting, the member needs to be able to see the listings they have created (probably on their profile page) with options to Edit, Upgrade a free listing, or Delete the listing.
View Templates need to be created for the free and Premium listing with custom sidebars to pull in applicable information (should be easy to do with the Views functionality).
A separate view needs to be created for those premium listings to be seen first and take precedence over the free listings.
I do need someone who has advanced WordPress skills and experience with the Toolset.