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One approach might be to look at a gallery module, like xcGallery or myAlbumP. Then you could see if you can modify templates to show the first two pictures in each category (a category for each student, for example).
Another approach would be to use a gallery (or whichever module you like), and create a single image from your before and after photo. In other words, turn two pictures into one larger picture.
And yet a third option would be to use any of the HTML wrapper modules (tinycontent, FreeContent, CJayContent, etc.) and create pages that look however you want.
Finally, you might look at WFSections and see if it let's you insert multiple images from the image manager. I think it probably does, though I don't know for certain.
I hope that helps.