How To Have More Fun With a Legacy

The only Legacy I play is Pinstar's Legacy Challenge. We can't play any other household in the town. So, that leaves out the rotation style of play, IF that's the legacy you're playing. That being said, focus on the Heir in each generation and realize each generation should have its own feel to it. It shouldn't be a repeat of the first generation, for instance. You're not dealing with the same Sims altogether. I agree with @Koteyka, don't make your Sims perfect, that leads to dullsvillle, which leads directly to boredom. Determine what your Heir needs to become successful, skills et al, and work on that. Also, make sure your Heir has a social life, of sorts. Future heirs are not created in a vacuum. Heir needs a life-partner. Heir must go out on the town to 'meet' the right Sim. Mix things up, have some fun!