I actually didn't do an actual "test run" for this challenge...I dabbled in careers to see which I could level the fastest in order to get the kids aged up. I wished I had done a serious practice run. It would have helped iron out a lot of bugs with my strategy. The bulk of my strat was done on paper. It looked something like this:
Jack: Technology: Military; Law Enforcement x2
Judy: Science & Medicine: Science; Medical
Ethan: Business: Nectar-making; Firefighter; Criminal x2; Business
Lisa: Communications: Alchemy; Investigator; Journalism; Politics
Arlo: Consignment sales; Writer
Darlene: Fine Arts: Ghost Hunter; Music x2; Culinary
Child #1: Part-time; Painter
Child #2: Part-time; Inventor
I paired by the Bunch Family with university majors because I planned on purchasing the honorary degree LTR so they would start at lvl 3 in their careers. I wanted a sim to do all the consignment sales & complete the consignment skill journal challenges on, so I skipped over physical education major in favor of this. I used the profession careers as padding before the normal careers to help store up lifetime happiness points needed for the degree reward & because leveling the skills would also help level the professions they were in. I decided to place the double branch careers in front of the single ones because when I would start the new career, I would be entering at lvl 5. Alchemy & nectar-making are careers you can easily max within a day or two by buying elixirs & nectar out the consignment shops & reselling them. The horseman career is another career you can also do this with. I choose painting & inventing for the unborn Bunches as I was unsure how quick I could capped off careers in order to cake them up & I wanted them to be able to start on careers asap...
The plan in action:
I started by selling their home lot & I moved them closer to the library. I wanted the money for elixirs, nectar & supplies. I sent Jack to China for the inn's book stash, dry food, some incense burners & a training dummy & worked on skills. Next, I sent Judy to France. She purchased the nectar books & 60k worth of nectar from the Nectary & worked on skills. I sent Ethan to the consignment shop with the nectar & Lisa to the alchemy shop where she spent the rest of the family funds into maxing the alchemy career. Jack & Judy worked on baby-making then parted ways to level skills (Judy also started a garden with red berry beans & bought a horse). Darlene worked on her cooking skill & Arlo on his writing. I capped the alchemy career & hit lvl 9 in nectar-making on day 1. I planned on picking Swimming in Cash for Ethan & Lisa's LTW. I sent Arlo to the alchemy shop (before caking up) where he dumped 50k into sales in order to pop their LTW. With the LTHPs, I planned on purchasing Mid-Life Crisis so I could re-roll their traits. (Bookworm, Workaholic, Neurotic, Ambitious - Lisa: Perceptive - Ethan: Brave). Capped nectar-making the next day & caked up Arlo & Darlene. Again, LTW was swimming in cash (another 50k sale dump) with re-roll traits: Arlo: Bookworm, Perfectionist, Neurotic, Ambitious, Born Salesman - Darlene: Bookworm, Workaholic, Neurotic, Ambitious, Virtuoso... When Jack & Judy saved up enough LTHP, I re-rolled their LTW to swimming in cash & did another 50k sale dump with a trait re-roll in mind of: Bookworm, Workaholic, Neurotic, Ambitious, Schmoozer.
Judy gave birth to twins, both girls, named Anna & Elsa. They also got the mid-life crisis treatment because I opted to keep them out of school in favor of career building. Elsa's traits: Eccentric, Workaholic, Neurotic, Ambitious, Lucky - Anna: Artistic, Workaholic, Neurotic, Ambitious, Lucky. Which ever girl finished their main career first would be entering the horseman career, hence the luck trait for winning races. They worked on the part-time careers together while doing their self-employed careers on the side.
At this point, my run kinda started falling apart. I got the flu & had a hard time focusing all the multitasking need to complete this challenge. I picked up the majors & the new trait: Schmoozer for Ethan, Lisa & Darlene...Jack & Judy: Genius. I goofed & entered Ethan into the business career without noticing until a couple promotions later. I think I also might have messed up my promotion cycles (every 3 days). However, I managed to cap the following careers:
Alchemy; Nectar-making; Military; Ghost Hunter; Firefighter; Investigator; Bookstore Clerk; Science; Grocery Store Clerk; Mausoleum Clerk; Law Enforcement: DNA Profiler; Business; Spa Specialist; Receptionist; Painter; Journalism; Music: Composer; Law Enforcement: Super Spy; Medical; Horseman; Gardener
Other things to note, I stopped playing my challenge early. I was too tired & sickly to use up my vacation days & I ended up leaving them... I ran into glitch with the Firefighter career, Ethan never wanted to go put out fires. They all disappeared whenever I tried clicked on them. I should have picked a different career path for Arlo. I was off on capping writing by a lot. Maybe Education with gardening, fishing & consignment sales as a side adventure. Inventing...I'm undecided if I could have capped it or not.