Typically I start with a female in CAS or a couple, then I move them into the world I feel like playing. I start messing around with store content, building lots, making houses, and just generally renovating the town. After that, I start playing the Sims, usually with a family as a end goal for that generation. I use the Tabcast to gain skills, I use alchemy to make friends if I'm playing a witch, and I like to meet lots of people or focus on a skill, depending on the sim. My sims will always have several dates before they get married, at least several, and I love to throw actual weddings. After that they get a vacation or an at home honeymoon, then I play them a bit longer before they have kids.
After that it's a matter of figuring out what to do with the kids, and then continuing on with the generational game,