Who Has Done Rags To Riches?

I've done one, it was the first generation of my legacy challenge. It was hard at first, but only because I was also doing legacy and had to have a family too. Even then it only took me less than a generation to make hundreds of thousands of simoleons, and that was before the gardening patch with seasons, which makes selling harvestables even easier. I found gardening and painting to be the most lucrative skills, but you can always try something else. I actually started a second rags to riches without the legacy challenge part, and it's even easier with one single sim.