I think it would be easier to maintain the media folders if the thumb's folder's were subfolders of each media folder rather than a sub folder of media
Example:
media/families/smith/
media/families/smith/thumb/
Since media can be resized with php, I'm not sure why there is a need for thumb's. Why not allow the admin to set the max width of displayed thumbs? The upload should be set to the max filesize or width of the uploaded image rather than the thumb.
Not sure if this aspect of image resizing can be done with php but in .Net if you resize an image for display, the actual file size (bandwith) is also redcued. Not having thumbnails stored on the server would also reduce server space.
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It's much faster to resize the image ONCE upon uploading that dynamically resizing it every time it's displayed.