With the painter, I usually have someone in my second generation become the first family artist. The founder is elderly when she gets her portrait, but it still counts. Also note that at level 5, the artist can do a still life, which can be centered on another Sim to make a portrait. Then at level 7, I believe, there is an actual portrait option and you don't have to position the camera because the Sim comes to the easel and you just snap the picture. Also, you don't need more than one artist at a time because he can use the still life option to do a self-portrait.
@LlamaMama: Those firemen are NPCs and don't have the full set of traits. It doesn't make them a bad catch, but they obviously will have less going on with their personality than a regular townie with 5 traits.
Leighton Sekemoto was my Dreamweaver founder's husband.