Holy cow! Well, I was feeling good about my score early in the challenge, but I ended up in 12th! (I finished with $503,451) It isn't a million, but I'd like to explain my strategy anyway. (With TL;DR length)
Yet another painter here, named Tomiko Kinsen. Her starting traits were Creative, Art Lover, and Perfectionist. She added Professional Slacker, Shrewd, Never Weary, Independent, Expressionistic, Hardly Hungry, Creative Visionary, Marketable and Steel Bladder throughout the challenge.
I chose to live on the cheapest lot in Oasis Springs. I built a tiny 2x4 room. I added a wall speaker (+1 Happy), the cheapest Environment 10 painting (+3 Happy), and a shelf with two of the reward lamps from Ambitions (+2 Inspired Aura). I didn't realize there was a higher lamp bonus, but looking at it now... duh! This combination of objects created a persistent +5 to Inspired. Finishing a painting usually gave a +2 Inspired moodlet, and an inspired shower or food took care of the last point. This allowed her to stay Very Inspired for the majority of the challenge with very little work. Outside the room, she also had the single bed with 10 energy and the cheapest possible need filling items except the shower, which was the second cheapest. I actually used items to fill needs... A fatal mistake, I now realize!
It didn't take Kinsen very long to cap the painting skill. I chose small paintings, as my testing had implied that they yielded the most value over time when paired with Perfectionist. I used Classical style until I was able to paint Abstract, at which point I switched. I horded the paintings as I created them, wanting to wait until I had Marketable to sell them. I did end up selling a few without Marketable so that she would have money to buy canvases. If she wasn't tending needs, she was painting.
Meanwhile, I collected satisfaction points by switching between Painter Extraordinaire (which she finished very quickly) and Fabulously Wealthy, and by fulfilling wants. I spent a lot of time canceling the same wants, trying to only keep the ones that were consistent with what she was already doing. (No, you may not plant something!) Even so, I derailed on filling wants a little, cooking and socializing more than was probably necessary for relatively little satisfaction. In retrospect, I shouldn't have given wants so much attention. About a week before the end, she finished Fabulously Wealthy, which was almost too little, too late.
My first priority for satisfaction rewards was getting Creative Visionary, and then Marketable. When she had both traits and a good number of paintings, I had her join the painting career. She sold off paintings to the art gallery and then quit her job, repeating the process when she had another set of paintings. She was in the Painting career for most of the challenge, but she didn't work a single day!
Kinsen subsisted entirely on garden salads, and incidentally ended up with level 10 cooking. I really considered going the pizza route, but figured it was impractical in the long run. I saved the dirty dishes in the Family Inventory until she could afford a Nanocan, and then tossed them one by one while she painted. Even at $10 a piece, throwing away those dishes added up to a small profit on the can.
She met Nancy Landgraab on the first day, and befriended her a bit so she could invite her over whenever she needed social. She would get Confident sometimes from finising paintings and rolled whims to use a bold pickup line. This ended in her having a bit of a crush on Nancy. She even asked Nancy to be her girlfriend a few times, but Nancy was having none of it.
On the last day, I sold everything she had. However, I did buy an oven and let her have a birthday cake. I couldn't bare to let her have a sad birthday after how far she'd come. If that shaved a few hundred off my score, oh well!
I am slapping my forehead over not making use of the needs potions! That is such a basic thing conceptually, but I tunnel-visioned on traditional need filling. And gosh, Loner is powerful! I'll certainly make better use of it in the future. I think I might take Kinsen and get her a family. She can get Nancy (an elder now) to leave her husband and move in with her to her empty lot! Haha. This challenge was a lot of fun, but if I never see another small, abstract painting, it'll be too soon! (But I'm sure I won't be able to keep away from painters for long.)
Maybe we should create a community hashtag and upload our challenge Sims to it? It could be fun to see/download the Sims everyone worked with.