show us your last sim that you made

That's similar to how Elijah started. Showed up in the city, used the cheats to buy him the lot with the gutted warehouse on it. He started with nothing at all, not even the camping stuff. Sent him out to gather stuff and sell it. Took a couple days of sleeping in the park and using the local gym to keep clean before he got enough to make some paintings. Sold them to buy the tent. Then he had a good place to sleep. More paintings bought him the cooler, cheapest table and chair. More paintings, lots more paintings, got him the shower. Now he had a place to sleep, keep clean and eat. From there worked on increasing skill in painting and did not too bad, couple thousand simoleons before the flea market showed up. That's when I discovered the street gallery he can buy and keep in inventory. That changed things dramatically, he can now make large canvasses of excellent quality, I think he is at level 7 painting skill. So he is well on his way now after about 2 sim weeks. Should be able to afford the lot in three or four days. Then it's more work on paintings to start to outfit it. Thinking of getting his loft fitted before worrying about the gallery part...better furniture and stuff will just make things easier for him. Plus the never weary reward, steel bladder and so on will make him able to really push out the art.

Rags to riches games are my favourite. I have had a couple where I imposed really strict rules on myself and made it very difficult. Probably my favourite type of game to play. The other challenge I enjoyed was the Room Challenge...great fun on that one.
http://forums.thesims.com/en_US/discussion/793808/sims-4-room-challenge/p1