With Susan opening her deli, I earned my first CaS sim, Nicholas Mason! Rolled a male, who'll get married. He got a fortune aspiration and will aspire to be an architect. Don't know if he'll achieve it in his lifetime, but I think story wise, an aspiring architect being the first to move to a new city, which is going to need buildings, is good thing ;) I haven't played him yet, just finishing up my first week with Zack, the last of the founders in my rotation, so I'll add Nicholas in after Zack.
I've never really been that good with challenges, but this really jumped out at me as something I would like. There's a LOT to it, but in general it seems "easier" than a Legacy, which I've tried and gave up on several times. So I'm going to give this one a go. 

I'm (basically) following the rules posted by iCad here - http://redmond-flats.weebly.com/original-challenge-rules.html and use a few of her rule tweaks as well.

One "rule" I've already decided to add, or more my own style of determining starting fund, is for now with a low population and only 1 comm lot, sims will get a randomly generated amount between 18,000 and 30,000. As the city grows, I will up the top amount in 5,000 simoleon increments as the population grows. First extra 5 at 1,000 pop, next 5,000 at 5,000 pop and next at 10,000 with an additional 5 for every 10,000 after. I figure as the town grows, there's a higher likelihood that richer sims would be attracted to living there.

I randomly generate numbers for just about every CaS decision; aspiration, gender, first letter of first name. I just go with whatever sim it gives me, only changing hair, eye color and clothes. I try to go with whatever sign it gives me as well, with only minor tweaks, but still keeping it within the same sign. I also randomly generate marriage; 1, they get married, 2, stay single. 

I choose to do the multiple founder variant and rolled 4. I made them all siblings (in my head at least, though later thought I should have made them as one family in CaS then moved them to a dummy lot and split them up so they could be siblings as far as the game knew as well). Their last name is Marshall, so naturally they called their new island settlement Marshall Island. You can read about them on The Founders page  /