Hey, I found a fun variant on some of these challenges, I don't know how to get it worked into Immortal Dynasty right now, but it basically is typing in:
FamilyFunds <lastname> 0
Every night. I wanted to play a game where poverty was a constant struggle, so I made a sim (Hungry H. Hobo, the H stands for Hungry), and said he could only start with his sleeping bag and one beloved possession, and was only allowed to get one new item each night. Every night at 11:59, I would sell everything he had beyond those few possessions, and all his cash would be stolen via the console.
Most fun I've had playing sims in years.
For the immortal Dynasty challenge, it might be fun to do something similar to this with the founder--when he would've "died" all but one of the possessions purchased with his funds/life work as an estate tax and drop the household funds to 0. I mean, honestly, for most veteran players, obtaining money isn't a challenge, this makes money a much more potent strategical component to gameplay.