Questions about the Runaway Teen challenge

So I'm finally bored with my Get Famous GP. I've played the same sim since it came out. He's a level 5 celebrity and maxxed the acting career and still can't afford a nice big house. It's ridiculous and I'm bored at this point. Anyway, I think I want to try the runaway teen challenge. I have never done a rags to riches type play where they don't start in some kind of apartment or cheap house but I'm ready!

I know there has to be a lot assigned to my sim even though he's homeless. What's a good lot? What neighborhood? I am going to have him literally start with ZERO money.

Is there a way to keep him from going to school? I guess I can just cancel the action?

Any advice let me know!