The *best* way to do this would be to have customization done to the store as per your conversation with John. Basically it could be in a combination of places, but most likely the image upload process would actually be either in a modified product questions spot or an addendum to the checkout process.

The quick and dirty way to do this would most likely still require some modification, but not on as horrible a scale...what I could see happening on the "fast and dirty" solution for this would be to do something like the following:

1] Make sure customer will be told that their order confirmation email will contain instructions on how to provide their image to you

2] Modify the order alert email to include a link to a special location where the customer can/will upload their image file and have the file name saved as the order number, or preferably uploaded and attached to an email sent to you referencing the order number

3] slight variations could allow for images to be uploaded to provide specific quotes if this is applicable, but in almost any case short of setting your site as custom and moving to our customer series servers, you will probably need to work with our custom programming department. They are all pretty sharp and can definitely get your needs handled pretty easily.