Regarding image syntax, would it be possible to allow an image to be a link elsewhere, but if not specified defaults to its image description page? On the main page, [1] could link to [2], which is the logical intention of that image being a link. Another example would be the Wikiproject Spoken WIkipedia sound icon [3]. That image, and others like it, aren't intended to draw you to the images page, but rather the project page instead. I think when you click on it you initially expect to be taken there, too.
[1] http://upload.wikimedia.org/wikipedia/en/5/5c/Other-langs2.png [2] http://en.wikipedia.org/wiki/Main_Page#lang [3] http://en.wikipedia.org/wiki/Image:Loudspeaker.png
/Alterego