Congratulations, ClayMask!
Thank you for explaining your strategy. It taught me quite a few entirely new things.
As for my strategy:
Isis Teague was a creative, childish, loner. Painting was her only skill. She lived entirely on moodlet solvers.
She made most of her aspiration points from painting and buying on a whim.
She purchased the 'connections' reward first and made money from entering then quitting all the careers. She wanted the special easel, and especially, the inspirational works of art from the painting and writing career.
I did not know about the 13 inspirational lamps - superb tip! She used only two of those lamps, and mainly got very inspired from hugging her teddy bear and viewing an inspirational painting.
She also purchased (in order): marketable, creative visionary, steel bladder, hardly hungry, morning sim and night owl.
The latter two were bought at a time where she knew that she had enough moodlet solvers to see her through. Obviously, she did not need these traits for skill boosting, but simply enjoyed the supportive moodlets when active.
She completed Painter Extraordinaire, Fabulously Wealthy and Mansion Baron.
Thank you for the insight in the workings of Fabulously Wealthy. I did not quite understand how it works and called it in too soon.
Isis never went to work, she just renewed her painting career entry (when needed) to sell paintings to the Art Gallery.
She only painted on medium sized canvasses and specialised in abstract, realism and surrealism. Her highest priced painting was worth over 14K. She was quite capable of painting 8 or 9 masterpieces in a row. Unfortunately, not every masterpiece pays out well. It was shocking whenever an excellent painting sold for more than a masterpiece.
She learned when to scrap a painting. A medium canvas takes in general 55 minutes, but this time can extend to 120 minutes. If the green in the bar doesn't move forward within 10 minutes, it is better to start anew.
I took an awful lot of screenshots and have written a commentary style story about this challenge. I'm currently doctoring out how to get it in a blog of sorts. But I wanted to stop here first and congratulate the winner.
Well done, ClayMask!