@abbyc97 I find that one of the best founder traits is 'loves the outdoors'. Starting off homeless, loving the outdoors is a great trait to have. I've been playing a rags to riches + legacy challenge combo....as I wanted an extra challenge of my Sims not being allowed to have jobs. I started the challenge pre-seasons, & I used collecting and gardening as my Sims money maker. Post seasons....gardening is a bit more challenging as not all plants grow every season. I would still say that gardening is a very easy way to make money. & I recently added floral arranging as a way to make money. Once your Sim levels up in skill, they can create some very profitable floral arrangements. I use the Yard Sale table, and start a yard sell at my Sims home lot, using a markup of 300%. So my Sim, makes $3K+ per arrangement. Also after obtaining 5000 aspiration points, my Sim was able to get the money tree. Maintain it well....and it's very profitable. My Sim gets about $16K per day from it. She just got her 2nd tree, which is currently growing.
All of this was of course over time....with having to skill up gardening, flower arranging, etc. But it has definitely paid off! My tip is to keep at it. Starting with $0 money, & no job....for me made this challenge so much fun. But I think with the Original Legacy Challenge, your Sims can have careers. So I would also add to pick careers that really payout....like Astronaut or one of the City Living careers.
Good Luck & Happy Simming :)