Imagecloud application

I am a designer (not developer) working on a design with a similar imagecloud as in bestuff(dot)com. I thought it was going to be a straight forward (if a bit complex) arrangement of thumbnails in css, but no its a single image with the borders and highlights added afterwards with css. My design is not going to be practical unless I can find a way to automate the procedure of creating this single image and producing the necessary css to arrange the rollover information and highlights.

How achievable is this?