Looking through the images I found Category:Images of Penny Wise and Category:Images of Penny Bassett. There is not the same issue with the Katrina Shanks/Shanks-Meltsner/Meltsner name switch, all her images are categorized under Katrina Meltsner. Should we simply use the new name for all categorizations (much easier, and keeps all files in one location, but you loose the data regarding the original name on the media). Or try to come up with a system to use multiple categories so we can keep the maiden name on the media and in the categories?
I'm leaning towards using only one name for categorizing. (As an aside when categorizing character images be sure to use the wiki's name, and not a redirect. Example use "Connie Kendall" instead of "Connie", and "John Whittaker" instead of "Whit", or "Mr. Whittaker").