Solution!

Top: Gregory Landgraab. The guy mentioned in that one Adventure career chance card. (He doesn’t look anything like his great-grandson… Malcolm + random template Sim)

Middle: Morgana Goth. The puppet girl. (I’ve bred her by mixing her ancestors, Cassandra, Mortimer & Gunther. I don’t know where she got these cheekbones from, though)

Bottom: Stella Livorno. She was a great painter apparently, and the lover of Malcolm I. Only mentioned in a Glamour Life Stuff painting. (She is a mix between Cynthia Kim, Jennicor & Nylissit Tricou)