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This is the challenge right?
http://modthesims.info/t/550861
I think you should be able to do the majority of the things in the Making Money section, if you set your town up for the challenge in advance. Sims can paint on a community lot and sell the paintings, freestyle and perform music for tips. They can't collect things, but they can dig up the lot and sell what they find, and make money by hustling pool. You can also set up a community garden that your Sim can visit. I would get the mods that allow skilling and sleeping on community lots to make things easier.