This looks potentially interesting, and quite challenging! Some generations will have a lot of goals to accomplish. If the point is to do everything in the game, though, I'm curious as to why you decided to go by main career rather than by career branch. Was it just to avoid the challenge becoming too long and difficult?
Also, a couple small things you forgot for A : Neighborhoods could include Anchorpoint Wharf in San Sequoia and infant food should probably include applesauce (possibly instead of smashed avocado, which could be kept for the S generation? I feel like it's easier to avoid forgetting things if, when it comes to things that show up in in-game menus, you go by the actual first letter.)
Anyways, I've created a family to try this challenge along with you. I created a starter Sim to be the parent of the first generation. Was that the intent? So far, I just have an angelic toddler named Alice who absolutely loves applesauce! She is also a Spellcaster from an Ancient bloodline, just because I wanted to throw that in and play around with it a little. I don't know if I'll share the whole process, but I'll be keeping a look on this thread to see what you come up with and make sure I don't forget anything!