I've taken three different approaches with my three (currently running) dynasties.
For Dynasty One, my Sim Founder married Billy Caspian and did Fishing. She had a wish of Surrounded by Family. Billy worked on Gardening and Cooking in between painting portraits and improving his painting skills. Heir was to be the Immortal painter, and younger siblings were to do gardening/cooking/painting/fishing. My gardening efforts were pretty bad in this one.
For Dynasty Two, my Sim Founder married Agnes. Sim Founder took on the wish of Renaissance Sim and did Fishing, Gardening and Guitar (I didn't do Fishing/Gardening/Cooking because I wanted another immortal to supermax cooking). Meanwhile Agnes did the Painting and the Cooking. I've learned a few tricks for dealing with the imaginary friend in this dynasty with regards to locking doors.
For Dynasty Three, my Sim Founder became very good friends with Billy Caspian, to the extent that Billy agreed to move in with him on day two. Billy adopted a female child who was going to take care of fishing and take over from her adopted dad for the painting. My Sim Founder married Meadow Carpenter-Rhodes who had gardening and handiness skills, as well as a puppy. I really lucked it big time with this one because both Billy and Meadow had their cars in their pocket. Founder and Meadow have had their baby, a girl, and a couple of days before she became a child, Billy adopted a second child, a boy, who I intend to marry the girl. Once Meadow dies (she has just become an elder while the founder (Chilli Peppers) is still a young adult) I'm going to see if my Founder can marry Billy's adopted daughter.
I have an idea of using the McDermott family from Riverview, if I get bored enough with these current three dynasties and want to try a fourth or something. I find that I try different things now instead of doing the same old things that I always used to do. It is all a learning experience, I'm finding, and that is something I enjoy doing, learning better ways of doing things in Sims 3.