Module for Premium Listings and Service Directory Including Payment

I am launching a hyperlocal news, lifestyle and events platform called NearSay this August. One of the ways we are looking to monetize the site is to create a self service portal for local businesses to be able to list themselves in a directory, reserve premium placements and take payment for yearly listings. Listings could be displayed by category (restaurant, bars, contractors, real estate brokers, etc.). Businesses should be able to log in and change their listings or update their service subscriptions.

Is there a Drupal module or framework that anyone recommends? Been looking around and found some options but nothing directly on Drupal and it would be nice to have a unified architecture.

Thanks for any help you all can give.

Trevor