Bulk email system

We are looking to set up a new system to request feedback from our customers, via the means of an html email. The data is to be collected from several csv files (all in the same format). Each import needs to be tagged a unique seller ID (e.g 23823411) which needs to be added to each sales record imported. We then needd to add the other fields to the table, request 1, request 2, request 3 and No request. We need to compare the information to two other exported data items, our address book and our feedback profile import. If any data is in the feedback profile import or our address book we DO NOT send them any email. Then we need to send an html email using details from the orders table. We need to send them a request 1, then mark it as completed, then a request 2, then mark it as completed, and then a request 3, but dont mark the box, so we keep sending request 3 emails. We also need to be able to search for an order by order ID and email address to mark the No request box. These emails need to be sent from different email addresses for each of the accounts. We need to be able to add new csv imports (email address and Seller ID) easily. If this is something you can do please let us know.