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I was able to work on some last night, I got Arachna, BeastkinBunny/Cat/Fox/Tanuki/Wolf done. What im currently doing is making sure that all folders are in the portraits/RACE/Female or portraits/BOBIES/Female, then im going through them and taking out all the ones I dont like (cause they dont fit my standard of quality) or if they dont belong there. Then im combining all the multi-age folders into their respected folders. Ex: If there is a folder labeled TEEN+ADULT, I would first go through that folder and sort the images, then I would copy all the remaining images into the TEEN and ADULT folder, then do this with any other multi-age folders. My final step is to then go through the 3 main age categories and sort the images aswell as remove any duplicated that I may find.

Actually the random portrait mod recognizes split age folders like teen+adult and applies both tags to them so they can be chosen for either.  There isn't any harm in splitting them up though and honestly I wonder how tied up it gets when it has to look through so many folders. I haven't encountered any performance problems personally.

I kind of wonder how the random portrait mod runs compared to how it is documented anyway. I need to pay more attention to what girls come up in game, because it feels like I see a low variety over and over. I know the characters are persistent and you can encounter them more than once, but I need to start looking to see what folders it pulls each character from just so I can assure my own paranoid that it works as intended.

Or I just have to start executing every captive.

I was experiencing the same thing, I noticed whenever i started a game up just to test out and ensure that the portraits were working, i noticed how the same 3-7 images (depending on # of images in the main folder) were coming up. But once i started to play i rarely encountered the same image twice, so im not entirely sure how the mod pulls images either.