I love this idea. But through my experience in translations, both on Transifex and couple of projects, this hasn't been discussed about before.
The way to do this is under each entry / important entry / misunderstood entry / confusing entry, there would be a link to the image in comment box. If this is true, and supported by the community, wow, would be a revolutionary in translation. Because of showing images/sreenshots for terms, not only good for translation, but it's also better in reviewing. But. When this becomes real, at least 500 hundred pictures (with the progress of translation in AOO 4x). A lot of people have discussed about this feature, some translators even suggested that "reeditting the code of pootle server to display image in the comment box". Well, this is a step further, at this time for Pootle Server and on their plan, Pootle Developers Group show no interest in this kind of ideas.