okay, I'll try again..
php - the scripting language that this forum is written in - typically has the ability to manipulate images built into it. It is possible to create a php script which you can call as an image file, and which will just return an image when called.
I use one such script to make thumbnails for my photo gallery.
The point is, that you could set the image to link to one of these scripts instead of to an actual file, and you could have the script look up with ship the person in question prefers, and send out the correct image file for that person. Only one style, a slight modification to the database, a slight modification to the signup and profiles pages, and 1 fairly straightforward php script and you're laughing.
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