Have you ever tried to play a “homeless” Sim?

I have, few saves. Recommend buying the smallest cheapest lot you can find and have sim sleep in tent and use portable shower or shower at the gym. I created an urban community farm lot (park) that I placed on the largest lot in Del Sol Valley so the sim can harvest and sell them, including tons of bees for honey. And since there are alien plants there it can be profitable. I have a couple of versions on the gallery. One with a bed and another with a tent. I did my 1st rag to riches story that way. After purchasing the lot I changed the family money to $500. Also helps if they are gluttons and they can rummage for food in the trash (once that bug is fixed) or you carry trash in your inventory, place it in the can and the sim can rummage for food in the trash. Then place the trash back in your inventory.