My spellcaster sims, Manager and Helper (wasn't feeling too creative with the names) moved into Bargain Bend in Willow Creek. They built a tiny home, and got all the quick aspiration points from Mixology, Wealth, Club, Collectors, Parenting, Spellcasting, eco innovator, vampire (research vampires on a computer), country caretaking aspirations. In totally, this netted to just over 1000 aspiration points for Manager. They then traveled to the Willow Creek Park, where Manager began completing the mischief aspiration while waiting for children to arrive. Manager was looking specifically for Billie Jang and Elsa Bjergsen, who have A's and B's in school respectively, but luckily they showed up pretty quickly. At this point Manager had started a club with the popular boost, and became friends with both Billie and Elsa upon greeting them - it did not take too much longer to reach good friends, especially as they were added immediately to the club so they wouldn't leave the lot. Once they were good friends, they were moved into the house.
Manager spent the rest of the day getting to L3 of the Mischief aspiration so she could purchase the connections trait and join the business career. Once this occured, she created a "fight" club to build an atrocious reputation (made faster by the tiny lot). She used this reputation to bribe her boss to ensure promotion in 24 hrs.
Billie, who had an A in school, got to work finishing the creative aspiration, and was aged up. Elsa did her homework + extra credit (and with the good schools lot trait) got to an A within 1 school day. She spent the rest of the time finishing the creative aspiration and was aged up shortly after coming back from school.
Later on day 2, a wishing well was purchased, and Manager got really lucky with an instant promotion on the first wish (after a $5000 donation). At this point, I could have finished the challenge by Tuesday 5PM, but realized it would be hard to set myself up for part II of the challenge, so I intentionally staggered Billie and Elsa going to school (one went on Tuesday and the other Wednesday) to reach an A grade. Manager went back to work on Tuesday, and got promoted to L7 at 5PM, and joined the Manager Branch, completing that aspiration. Once finished, Manager learned an instrument to mentor Billie and Elsa.
Helper helped out by also learning an instrument to mentor Billie and Elsa, and also her magical prowess so that she could learn copypasto (for the potion of plentiful needs and nimble mind potion. This happened around day 2 or 3). Finally, in the background, the rest of the club spots were filled up by L and Simeon, who helped Helper grow her magically prowess and diligently painted the entire time, and had their paintings stolen and sold by Helper to provide a sustainable stream of funds.
All requirements were met shortly after Elsa returned from school on Wednesday at 3 PM, and both Billie and Elsa were aged up (which took about 12 sim minutes - I also missed
@Elinoee's questions - though fortunately it did not come down to a tiebreaker for me
).