Cool thread idea! I really like your story about Olivia. It's interesting how you came up with her character idea, but then started over and actually played out her backstory. Seeing her finally in her original outfit style made me grin. You made it feel very natural.
Whenever I start a new game with a new sim or new set of sims, I usually play for about three to five sessions with them to see if I bond with them or not. If I do, I may end up playing with them for years. If not, I generally quit playing with them.
Maybe it's because I easily feel empathy toward made up characters, but whichever sims I have been playing with the most, most recently, start to feel like the most special ones. So it's hard for me to say who would fit into this description best for me.
