Dynamic Quantity

Is it possible (or would it be possible to add a feature) to set the allowed number of files for each instance of the Upload button depending on the quantity of an item in the cart?

For example, I have in my cart an 8×10 photo print, so 1 photo is allowed to be uploaded. If I want to order two 8×10 prints with a different photo each, could the same upload botton allow 2 photos to be uploaded this time?