The game doesn't do story progression. What I did is left aging off for a while, and rotated play between the Caliente's, the Landgraabs, the Goths, the BFF's and the Roomies and make sure they all had some kids. I also went ahead and married two of the BFF's off to each other. Then I kept playing my family for a while till the babies aged up. Once the babies aged up I moved all the richer kids into two boarding schools.
I repeated this again and had some of the families have more babies. Now that there's tons of kids to take over when the parents pass on, I turned aging back on and mostly just play my family and the two boarding schools here and there.
Here's what my towns looked like last time took a screen shot. There are now more kids in each school and some of the young ones are teens now. I'll update this again in my profile later. :) it seems like a lot of work but it's actually really fun to play the whole world.
As you rotate you can also have parties and this helps to make sure all the families in the worlds react to each other. Sometimes when you get back to a family you find out they've had some affairs. Lol.
