Maybe support multi-portrait editing in this manner:
shift+ctrl-click to select multiple. Once multiple are selected, all checkboxes get unchecked (once initially going into multi-mode). After that, checking boxes, and and clicking apply, it looks at each, and each section that has something selected, it applies that to all the files?
I still want to allow picking non-standard colors for races, as you can modify them via dye's etc., but did think about changing their color to red to signify they're not a standard color for the current race(s).
Agreed on shifting the file selection, the portraits are mostly vertical anyways so there's extra horizontal space. So move that over, then maybe stick the portrait photo above it or something so you see both body and portrait?
I was also thinking a filter for the file list, can type in text, and it filters the list to only items that match it.