Donna:

You want to put an item on an order and have an image printed on the order document (detail section) based upon that item? More than one item and/or image?

Possible, but I believe the images have to be a consistent type, size, location, and naming convention.

PrintBoss Standard is $495 but I almost always end up needing to use PrintBoss Enterprise at $795(USD). There is a demo version available.

The cost of services to get this to work is another matter. I would classify this project as requiring an very high level of expertise in PrintBoss. I would be happy to offer the service of my firm, please feel free to contact me.