Like ClayMask, I also did the Computer Whiz Aspiration, but mostly because I knew it would be a lot of easy fast forwarding. A lot of my choices in this challenge were motivated by how much real life time I would have to put into them.
While I did give myself 5 of them for some initial funding, I avoided buying the Landgraabs and SKLs weight worth in violins (and when I sold my violins I made sure it wasn't on Fabulously Wealthy- still counted, though) because it honestly felt too exploity for me. I earned that aspiration by having my spouse, the two adopted children who stayed with me, and another helper (originally a gardener before I decided gardening would take up to much RL time) paint up a storm.
One random thing I noticed- part of my strategy was taking a gym trainer as my spouse to have someone to mentor my sim in fitness. While befriending sims at the gym I noticed that Don Lothario had become a gym trainer, and was able to mentor me. Since I know Don is nowhere near level 10 fitness initially, I moved him in out of curiosity and found that the game had maxed out his fitness for him. Just something interesting I though I'd mention.
Violin Fashingbauer (one of my baby boomers) celebrated the completion of the challenge with a whole household dance party, then a quick rush to clog some drains because I had completely forgotten about that. Ironically, she never even picked up a violin.