I appreciate the help. However, I was thinking of how eg Jane/Kylie have the "Bimbofied" personality, and their base portraits change. I've seen the same with the other characters, but I'm not sure what requirements need to be met for this to happen.
There are "bimbofication:true/false" variables in the save file that when toggled triggers this change, but I've yet to pin down how/when this happens. So far, Kyle and Jake (maybe Heather? Don't remember) are the ones that have been triggered without me fiddling with the variable. Some characters have the personality "Bimbofied", some have "Bimbo", and I'm not sure a) what the difference is, and how/who the different ones apply to, and b) how these different "flags get set", for lack of a better word. Not sure how I got the Jake and Kyle ones to trigger, and not sure how I would go about triggering the other ones.