Had a lot of fun with this one. Priority was to get all the positive influences possible on to painting values (skill, character traits, easel quality, lot trait, aspiration rewards) and just churn out as many paintings as possible for the RNG to provide high values.
Barbara Art (named after my favourite artist Barbara Kruger) is Creative (for inspired mood), Perfectionist (makes higher quality items), and cheerful (mood boost). She moved into Pebble Burrow in Oasis Springs with the lot traits natural light (to boost painting skill learning), home studio (for better quality paintings), and study spot (boost to all skills). She built a 5x2 microhome for the skill and relationship boosts. Inside were two rooms one with toilet, one with shower. Outside we had a bookcase, chess table, stereo, some extra seating, and of course an easel.
Step one, as with so many challenges, join the Good Timers for the Rally the Troops club perk. This was changed to the Art Timers (although Barbara was the only one who did any art). Members were swapped out for townie singles. Club activities were chess, dancing, being friendly, reading books. These were swapped around occasionally as needs be - for example showering to avoid members leaving the lot. The club was almost always on throughout the challenge. Perks bought (not in order) were Networked club (for promotions at work), inspired vibes up to the max, one level of romantic vibes for dates, painting skill boost, logic skill boost.
Priority for day one was to get enough aspiration points to buy Connections to get a boost to starting the painter career. This is because the best easel, Deluxe All-Season Easel, is a career reward for level eight Master of the Real branch. Barbara switched between aspirations; Painter Extraordinaire, Soulmate (hence making a club of eligible singles - Nina Caliente turned up feeling flirty so they wooed and married day one), Renaissance Sim (first level only), Leader of the Pack, Family ones (just the 75 points for spending 1k on childrens stuff), and Fabulously Wealthy. Plus want points for listening to the music she likes and flirting/ being friendly etc. She got the 3000 points by Monday afternoon so that her first day at work as level 4 painter was Tuesday. Of course we would also buy the wishing well and time wishes for promotion so that she reached level eight in good time to spend most of the second week painting. This is also why the chess tables as the career required some logic skill. The wishing well is also risky so I was lucky that all the wishes were positive or neutral which didn't slow the career progress.
What was interesting was that the first five or six masterpieces on the Deluxe All-Season Easel level eight easel were all lower value than my top five or six from the Easy-Breezy Easel (career reward for level four) so I sold it and bought that one again. But then I swapped back with a few days left and am glad because that's when I got the top few valued paintings. I tried painting in several locations but none matched the home one with the lot traits so club members were rotated out once I had a high value portrait of someone. Bjorn Bergsen had five or six paintings of him done and none were much value. Johnny Zest's portraits were higher value when he was frowning. Dominic Fyres's portrait, despite not looking thrilled at posing for it, came out with a 9k value painting on first try (with the Easy-Breezy Easel!). It was interesting to experiment but the main thing was numbers.
Even with top skills, traits, and easel some masterpieces were still coming out valued under 4k so Barbara was kept busy, painting day and night - 64 eligible paintings in total. She only went to work when a promotion was due and then used vacation days.
Barbara's top 10 paintingsSalim Benali 10,688
Nina Caliente 9,743
Johnny Zest 9,464
Justin Delgato 9,398
Dominic Fyres 9,336
Zoe Patel 9,003
Agave Abode 8,586
Diego Lobo 8,200
Nancy Landgraab 8,126
Supriya Delgato 7,138
Hope that's enough info. So much relied on chance with this one I'm sure many other participants had an identical or better strategy just not as good luck.