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Thatd be sweet if you would! If you want we can work together to get the pack all nice and organized, aswell as trim out the bad ones. I just dont have the time to go through all 3700+ of them and trim them.

Yeah that's a good plan.  These ugly pictures would be fine if you could link a portrait to initial appearance,  but since you can't (unless you set it manually, and that's no fun). It probably could be done actually but Im not sure I'd rather just delete the uggos.

I'm getting rid of
-Furry in non furry folders

-Split race folders

-Characters who look weird to the point of being alien

-Most CGI images

And keeping all the cute anime girls and even the cute western style girls.

But its not something that will be done today as I also have to go to work.

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.