I didn't come into the franchise until late into TS3, about a year or two before Supernatural released. I downloaded TS2 when it was free on Origin and never really played much with the premades.
That being said, I still feel a bit nostalgic about older sims even though I never played any before TS3. I guess it's because they're referenced so often in the community that I feel like I've known them my whole life, if that makes sense.
I have recently started playing TS4 premades, and I have added (I think) all the premades from Strangetown to StrangerVille. I evicted all the premades from StrangerVille, except George Cahill. I actually just rotated to the Grunt family but I haven't had much time to play them yet.
I kind of want to go back and play TS2 to get more familiar with their storylines.