Email Automation

Need to set up an email process that prepares and sends a series of 20 emails that relate to two dates: the date we sign them up, and a specific future date identified by us. For example: Signup date: Email 1 Signup date +5 days: Email 2 Signup date +7 days: Email 3 Future date -21 days: Email A Future date -14 days: Email B Future date: Email C Future date +1 day: Email D Each email will contain unique information taken from the initial form we fill out and that you need to create. There are about 22 unique fields for the form that need merged into the emails before they are automatically sent on the specified date. A copy of each email must be sent to the administrator email address also. I would prefer to use Outlook as the email platform (using its delayed send function), and married with any Microsoft office product if needed. MailChimp is also a possibility, but not preferred.