It does look daunting, but once you get organized, it actually is fairly easy (time flies!).
What I did in mine is lay out ahead of time which generation does what skill and career, and then focused on that. I do recommend unlocking Charisma skill, and when you can, purchase the Attractive LTR. Once you complete the first Charisma skill challenge (where you have 25 acquaintances), and you add the LTR, you become instant friends with anyone you walk by. Don't be afraid to enslave abuse put to work the spouses/partners. They're a great source of help!
As an example, since I knew ahead of time that I wanted generation 6 to be an inventor, and to get her LTW of Monster Maker, I was able to spend all of the previous generations hunting up 30 Life Fruit, 3 Heart Shaped Pink Diamonds, and 3 Palladium Bars. She literally finished her LTW within 2 days of turning into a Young Adult.