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I think limiting the number of children is useful. When they graduate everyone in the family with a rabbithole job misses a work day.
Ambitious + Workaholic + Multi-Tasker LTR works wonder for rabbithole job. Ambitious also does double duty here for the extra lifetime happiness points.
Just offhand, other than a Private Investigator, what other professions are rich in opportunities? I've gotten about 8 from PI, and I know there's a few more, but I keep getting the one to Study, or repeats of old ones.
EtnaFan, did the skill challenges your sim completed at University stick? I've heard about skill challenges completed at University not transferring over when your sim returned home, but that was all the way back on patch 1.50 and I'm wondering if things changed.