And how do you identify the image for each contact, based on what, on the email address, user_id or what exactly? Is that field part of the email list fields?
We can probably export and re-import the contacts list with an extra link field, so each contact would have an ImageLink column.. and the link would be something like this: https://mysite.com/userimages/asdfsadf1.jpg (each contact would have his/her unique image)