I hope to clear most, if not all, of the skill choice confusion up soon. I'm going to lay out exactly what I intend to do—at least give players a taste of the first 3 generations. I'll be very specific and leave no stone unturned. So, hopefully, that will help. I'll do that later today, but need to get to some house chores first.
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EDIT: Okay, here’s my walkthrough for the first 3 generations. Whether or not I actually do this is up in the air, but for now it sounds like a solid plan:
My Founder is Moe Howard. Moe’s going to marry quickly as TheCub correctly pointed out—you can’t dawdle on getting the paintings done. So, Moe marrys and his wife will assume the responsibility of painting Moe’s portrait, and also doing the photo and ice sculpture. She’ll be quite busy.
As for Moe, now that I think about it, guitar is not the way to go. I’ll have Moe go the Science career route and that way the gardening and fishing necessary for making Ambrosia can be taken care of, plus he’ll have handiness to to repair things that break. So, his LTW will be the Creature Robot Cross Breeder and his wife will essentially be the cook and a self employed painter, sculptor, photographer.
Moe and whatever her name will be have one child, Shemp. Shemp’s the 2nd generation immortal. Moe will probably have maxed gardening, handiness and fishing, so all 3 skills will be off limits for Shemp’s supermax choice. It would make sense for Shemp to become a da Vinci because Moe’s wife won’t be around very long to handle the paintings, photos, and sculptures. So, Shemp will pursue painting, sculpting and inventing and his targeted supermax skill would be one of those. His career will be a self-employed profession. Shemp’s wife will need to get in on the act as far as painting, sculpting and photography because Shemp will need his own objects for the museum. But, once Shemp’s wife is gone, then Shemp will be able to handle all museum objects for all future immortals.
Shemp and his wife bring in the 3rd generation with Curly Howard. Woo woo woo woo. Curly needs to pick a LTW, career, and supermax skill all different from Moe and Shemp, so let’s just say....a Swimming in Cash LTW, a Ghost Hunter career, and a Logic supermax choice.
Death Fish and Life Fruit can be kept indefinitely in inventory without fear of them ever spoiling, but there's still the requirement of someone with a maxed cooking skill to make the Ambrosia. So, I may just have Moe assume that responsibility and be the Dynasty household cook.
It is a little confusing in the sense of how many ways you can approach this, but I hope this example at least clears up some of the skill/supermax choice confusion. The bottom line is you'll have 8 immortals which means 8 different supermax skills, 8 different careers (rabbit-hole or self employed profession is fine) and 8 different LTW. Just plan it out for yourself and that will avoid confusion down the road for you when you get to generation 5 or 6 and are wondering what your remaining immortals can choose from to fulfill their requirements.