Email clients based on previous orders

Use current database, and order details to pick out customers who have bought certain items and send them a email in a mass format. Would be good to to this via Hotmail account and to use outlook as email handler. Need to pick certain SKU’s individually or combined to derive email list based on the criteria required. Email out need the ability to attach pictures if possible not just text based. Also need the feature for the system to pick out customers only within a specific date range for the above task rather than all our customers in our database.