Pretty straight forward:

Create only one, ya/adult sim and move him into an empty residential lot in a town that's populated with other residents and fully furnished houses.

Rule: You're not allowed to enter buy mode and buy anything from there until you complete the challenge's goal/objective (While you're not restricting from using Build Mode and building anything).

Goal: Play it until you run out of items to steal (basically leaving everyone in the town homeless, or shall I better address it: furniture-less.

Feedback, stories, and critique is appreciated. As I disclaimer, I haven't play tested it, but I theorize it should work. Should also probably be base game friendly/compatible.