Plugin help for classified ads marketplace

Hi Folks,

I’m wondering if you can help me understand what plugins are required for the following website requirements:

• A product marketplace where vendors can post classified ads to showcase their products
• Each classified ad costs X dollars, and runs for Y amount of months
• Upon approaching the ad expiry date, the vendor is sent an email to remind them to renew the ad for another Y months if they wish to
• Each ad must be posted under a product category, and optionally a brand as well
• Optionally, different ad levels could be created. Each ad level gains more features (e.g. listed first in category) but costs more to be listed

Help appreciated.
Steve