One of my favorite things to do is a rags to riches type challenge. My most recent sim I put into a crappy apartment in San Myshuno, deleted everything that wouldn't naturally come in an apartment (I left the fridge, toilet, counters, sinks, shower, and a crappy couch because I figure people leave those out free on street corners often enough) and then reduced her money down to zero. Then try to make enough money for her to make a living. Originally I wasn't going to let her have a job, but my game seems to have a bug when it comes to selling photography in a retail store, so I gave in and got her a job anyway. But I have done it with just collecting, writing, etc. It's nice that it gives you a goal (currently I want her to complete mansion baron and buy a super nice penthouse in San Myshuno). I got the idea from The Sim Supply on YouTube if you wanted to check out his videos.