Gm Upload Portrait Issue
So...
I have successfully deleted an NPC without their portrait being removed, then deleted the portrait, uploaded a new portrait in that slot, and selected that portrait with a new NPC.
I have removed a portrait from an NPC, uploaded a new portrait in that slot, and successfully selected that portrait with a new NPC.
I put an uploaded portrait on a PC, then moved them to hidden without changing the portrait, THEN deleted the portrait, and successfully uploaded a new portrait in the same slot for selection for use by another PC.
The only thing I haven't tried - because I'm not willing to dink around with other players' characters - is altering portraits on PCs that belong to PCs that don't have GM access. I can't break it with anything I've tried, NPC or PC, removing or not removing the portraits before replacing them, but the only characters I've attempted to manipulate have been characters that belong to players with GM access.
...just to ask the dumb question, silverelf, but you definitely checked the 'delete' box under the image, and then hit the 'Upload Portraits' button to remove it, and then went back in to 'Choose file' for the new image, and then hit 'Upload Portraits' again, right?