Using standard installs of Drupal or Joomla:

Build a plugin that will automatically create the infrastructure from a list specified by the user. List could be state names or city names in a state or county names.

Allow dummy listings to auto-populate with user-specificied variations in each listing. Dummy listings can be deleted by hand or turned off altogether.

Allow for featured listing in every category or a site-wide featured listing that will stand out.

Might need to create a Template.

Can be a script or some MYSQL script. You tell me.