I'm going to end my game at 6:17 am on Day 100. Yes, I know I have a few Sim hours left to make more money, but I'm solidly in third place, and I won't beat Mooner in that time so:
Lifetime Happiness Points: 387,431 (The Ambitious trait really did pay off here!)
Net Worth: 1,698,971
In case y'all are interested, I started again with a second Sim (I do that a lot). Ambitious, Loner, Artistic, Bookworm, Green Thumb. Working on the gardening did pay off, because I ended the game with six bearing Money Trees and a whole whack of Omni Plants that were producing the most expensive book. For about an hour's work, the garden was producing about $10,000 per day. As a writer, he specilized in Children's Books, because although they're almost as short as fiction books, they result in $700 to $900 royalty cheques, and he didn't need to wait until he was a level ten writer. Once the twenty book mark was reached, he could write three or four books a day, and after the first twenty books, every single book was a best seller! In between books, my Sim would paint, so eventually he would steadily produce three large paintings, three or four children's books, plus the garden income.
Anyhow, thanks for the fun challenge!