So I think I have it all down now, but just to be sure, would this chain of events be within the rules? Note, this probably isn't the path my dynasty will follow - I think I need to do a bit more planning yet.
Gen 1 immortal: Takes up painting as a career and the skill to max, he reaches level ten skill and job wise and does all the associated challenges. He also reaches level 10 in handiness, but fails to complete all the challenges.
Gen 2: Takes up sculpting as a career and skill to max and thus reaches level 10 in job as well as skill and completes all challenges. Along the way he does some gardening and reaches level 10 of the skill, but does not complete all the challenges.
Gen 3: Takes a science career and along the way maxes gardening, fishing and handiness. He completes all the challenges associated with gardening and therefore takes this as his super max skill, but does not complete the fishing and handiness challenges.
Gen 4: Heads into the culinary career and along the way maxes the skill and completes all the challenges.
Gen 5: Goes for a professional sports career and so chooses the athletic skill to max. He dabbles in a few skills, but doesn't complete all the challenges for any except the athletics ones.
Skip to gen 8 who also dabbles in a few things and maxes a few skills like athletics and fishing, but fails to complete all the challenges. He takes up martial arts in his spare time and chooses this as his skill to max and complete all challenges for.
Norma