Wow...what an in-depth challenge! I told myself I won't try this, as I'm just getting to the end of generation 2 in my Life States Dynasty and trying to write up a story, but it's hard not to get sucked in to theoretical planning.
A question: I see in the rules that "moving heirs" (#4/8/12) can pack up and take their career rewards with them. What about Lifetime Happiness Rewards? For most of these, they are just benefits that will stick through a move as do skills. But what of object-based LTRs, such as the Collection Helper or Moodlet Manager? Do these travel with the moving heir?
On the subject of moving heirs (and in the absence of a Tips thread for this challenge) - It seems to me that one of the most important choices is which careers/skills to choose for moving heirs, as their abilities might make all the difference when starting afresh in a new town. For instance, leaving something lucrative like Painting for a moving heir, thus allowing them to start in a new town with level 10 painting right away and the ability to crank out masterpieces... or perhaps having a moving heir maxed out in Chemistry, thus allowing for Sleeping Elixirs for themselves and heirs in the new town right away... It seems to me that various skills or career awards (laptop, fridge) might be very advantageous to the generations in the fresh town.