I need gameplay ideas that are fun and chaotic, yet long term

I do a Rags to Riches, but with a twist -- I have a runaway teen living in the cheapest San Myshuno apartment s/he can find available (sometimes I'll kick Salim Benali out of his place into Not In World population). They have to earn money while trying to get their grades up through a combination of finding collectibles to sell, crafting items at the Arts Center (like paintings or woodworking sculptures), and odd jobs. I don't do a part-time job because I like the flexibility the odd jobs provide. I get the apartment, then I take the money left down to just one week's rent (just to give them a cushion), but then they have to make it on their own. And I don't age them up until they've completed their first aspiration; I pick one that doesn't require them to be an adult, like the creative ones or the outdoors ones. Since the teens make money by collecting The Curator can be a good option for aspiration. B) The painting one works well too once the teen has built up a small financial cushion so they can afford the canvases.