Coming out of lurkerdom to say this challenge looks awesome. My least favorite part of Sims is building a house from scratch, and I love that this challenge lets you really explore a town and get to know all of the houses and families.
I read all the rules and got one started, and realized I was a bit over my head. I started with Hank Goddard and Pauline Wan. I had Hank and Pauline throw a bunch of parties and make a ton of friends. I changed Hank's LTW to Super Popular. I made my heir a loner, hates-the-outdoors, bookworm, and got her working on the writing skill. Then I realized, I'll need Hank or Pauline to die before my heir can move out, and then I'd lose half of the household's friends. (Duh.) I've kept going in the game I already started, following more the spirit of the challenge than the actual rules.
I love my heir too much. She's married Sam Sekemoto and just gave birth to the second heir. I feel like I'm invested in the whole town rather than just one family, and it's been a lot more fun.
I will start a new game and stick to the rules. I think I'll have my first heir super max out charisma, so then he/she can have all of the friends and I won't have to worry about relationships dying with a family member. What families does everyone like to start with? I thought picking a young couple would be smart, but I could see why that would be difficult, too. I'd hate to be done with all the requirements, waiting around for a sim to die, praying that my heir's fiance doesn't become a vampire.