I've been playing this challenge for over a year now (off and on), and am in the 1970s :) (accidentally skipped most of the 1920s due to some heir issues/confusion). It's a lot of fun, but I started it before I had ANY expansion/game/stuff packs, and since then (especially with Glamour stuff and Get Together) things have been added that I think would have really enhanced certain decades. So now I'm planning on finishing it, then restarting the game in a new save/new characters. Really looking forward to it!
And @CuteCoffeeGal , I'm looking forward to checking out your videos and thank you for elaborating more on the challenge rules!
One thing I wanted to add: Since Get To Work added sickness, until maybe 1920s?, an added difficulty could be that every time your Sim gets sick, you roll the dice to see if they live or die. I may or may not do that, but I thought it might add more tension.