That's going to require a little more in depth analysis, and development, to determine and acheive your specific requirements.
1) do you want to save the image, so it will display on cart summary pages (shopping cart, checkout, etc.)
2) should it be stored with the order (the image)?
Yes, it would be a good idea to start with the XmlPackage. You may need to edit or create custom XSLT functions/methods to assist you.