In my current attempt, I've decided to keep Painting as a free skill because
1) It can give my elders something to work on once they are elders and
(Gens 1 - 7 supermaxing painting)
2) It is part of a number of LTWs that I like to complete, an
(off the top of my head: Renaissance Sim (not necessary, but I like doing this as one of those ones), Master of the Arts, Illustrious Author, Descendant of Da Vinci, and Visionary).
3) i like the animations they go through with painting.
Gen 1 supermaxed Street Art and did street credible LTW with the forgery track of the art appraiser career.
Gen 2 is supermaxing Sculpting with Descendant of Da Vinci LTW (she used brain enhancing machines for inventing) and Self Employed Sculpting Career
Gen 3 will supermax Photography with Visionary LTW and Self Employed Photographer Career.
Gen 4 will supermax Handiness with Monster Maker LTW and Self Employed Inventor Career.
Gen 5 will superrmax Alchemy with Alchemy Mastery LTW and Self Employed Alchemist Career.
Gen 6 will supermax Gardening with Renaissance Sim LTW (Painting, Gardening & Cooking) and Self Employed Gardening Career.
Gen 7 will supermax Fishing with Master of the Arts LTW (strange combo, I know, but ask anyone who knows me, and they will tel you I am strange) and Self Employed Fishing Career.
Gen 8 will Supermax Writing with Illustrious Author LTW and Self Employed Author Career.
Gen 1 hubby (Gobias) did handiness, gardening, fishing, and picked up a point of alchemy. This was in order for him to get to level 5 in science career, and then go into the SE Gardening, SE Fishing and SE Alchemy Careers for his LTHPs (his LTW was to hit level 5 in four careers), he chugged a Wish Enhancing Elixir and bought the family a food replicator reward. He also caught enough deathfish, angelfish and alley catfish to stock the pond and Grim came for him just after he caught a deathfish. He also upgrade items, especially the food replicators. He was extremely fortunate with his garden - several money trees, life fruit trees and death bushes from the special seeds he found.
Gen 1 helper 1 (Victoria Andrews) did painting and was basically responsible for a lot of the raising of Gen 2, in between her job (which was the basis of her LTW). She achieved her LTW which was to hit the top of the journalism career and also wrote a few books for later generations to read. She died just before my founder hit Elderhood, which was a shame, but my back up was in place. I believe she also picked up a food replicator reward for the family.
Gen 1 helper 2 (Beau Andrews) did sculpting, photography, cooking (all from the brain enhancing machine - I got him to the level to do ice sculptures and then his first 25 sculptures were ice) and ha his LTW changed to Renaissance Sim. At level 10 cooking, he went to the bookstore and purchased himself cooking books, 2 of ambrosia and 1 of all the rest, he read ambrosia, and made it to the mixing bowl stage before stopping and storing it into the upgraded food replicators. He also purchased a collection helper from his lthps). As with Victoria, Beau died just before my founder reached elderhood, and as with painting, my back up plan was in place.
Gen 2 and her husband both did painting and sculpting. Husband focused primarily on Sculpting (he would be the one who would end up doing the Founder's Elder Ice Sculpture and all of his wife's sculptures), and Gen 2 initially focused on painting (to do her mother's elder portrait. Hubby also did photography.
Both of them had imaginary friends who were turned real, the female IF took over gardening and fishing and the male IF went into alchemy and dabbled a bit in science and writing as well.
Gen 3 and her future hubby have both been born and are toddlers. As she is supermaxing photography (and I will have a backup when should something go wrong with that skill) her hubby will also learn photography to complete the photos of Gen 3 after the Gen 2 spouse dies.
Pregnancies and Sculpting
I am playing without Seasons, Pets, Island Paradise or Showtime (I didn't get them for my laptop) and so snow days and days off for celebration days do not impact on game play. So, the biggest thing that dictated when I made my sims pregnant was - Beau's progress with ice sculptures. When he got to 20, and I saw there were still a few days before my founder reached Adult, I sent all four adults to their bedrooms. As I wanted both couples to give birth on the same day, I had them do the romantic interactions early morning and chimes were heard first time for both couples. I did the same thing when Gen 3 and her future husband were born. I do that to avoid multiple days off for high school graduations as you can't age up early in this challenge, so the control you have is dates of birth for heirs an spouses and heirs.
Photography Skill
With Beau I just simply got him to level 10 photography skill and had him take the photo of my founder, I was more interested in ensuring it would get taken than with values of his shots. I did send him regularly to the consignment store to look for those most expensive cameras, which I think he got on the second or third try. I also had Gen 1ers pick up things and bring home that would be useful for future photographs.
I gave Gen 2 spouse the lovely camera and he went around the yard photographing the stuff his parents and in-laws brought home and then the various buildings and sights of Sunset Valley. I do want him to get to 75 shots for that bonus and also to photograph 10 landmarks for that bonus before anyone goes anywhere. Once Gen 3 is a teen, she and her parents will be off to France so dad and daughter can get photos of the sights of France, especially the nectary. I will follow that up with trips to China and Egypt for the same purpose.