My main strategy in this challenge was to try to avoid careers as much as possible so Sims had more time to skill. I used Nutella's strategy for gaining aspiration points through cooking. I also went back and looked at last year's Skills Dilemma challenge and read what the top players did to gain skill levels quickly.
Main Household:
My starting Sim never had a job. From Sunday morning, to Monday at 5AM, he cooked. I cancelled other whims so that he would roll cooking whims. I also bought things he rolled a whim for (lots of 1X1 pools, ice cream makers, drink fountains, and hottubs). By Monday morning he had enough points for Connections. He also had L8 cooking and gourmet cooking and L3 Mixology from making Prose and Pop for the inspired mood. I was initially not going to do Mixology, but since he already had 3 points, I kept it. He then focused on skills he could mentor other Sims in--logic, piano, and writing. By Saturday at 11:25 AM, he completed the Renaissance aspiration. He bought the Savant and Observant rewards. I got observant so that he could easily find out the traits of Sims moved in by the game. So, once his aspiration was complete, he visited all the Sim families in Willow Creek that had moved in and found out their traits and careers. In my practice, I found that if you moved in when a Sim was supposed to be at work, sometimes they would be at home and would take a big performance hit. So, I had my Sim wait until early Sunday morning to move in with his first family. While he was waiting, he continued to work on maxing mentorable skills. He gained logic by painting mathematical diagrams and stargazing so that he could take the focused items with him from house to house. He also dug up a few crystals for the energized mood. Cloudgazing, Prose and Pop, Plunk or bow for inspiration, plus a Lavendar soak bath easily got the very inspired mood with the knight's armor and the laser show environment boosts.
Every house I moved into was bulldozed and replaced with a couple of bathrooms and two large rooms for skilling. The bathrooms were only used for taking baths with soaks.Moving around in large houses or houses that have multiple stories takes too much time.
Family 1: Jaden and Yesenia White
For every family, I had the same basic strategy. One Sim never held a job and I used cooking and gourmet cooking to get the points for Connections. Other Sim(s) did get a job, but as soon as they had enough points, they quit and also got the reward. One of the jobs I relied heavily on was Criminal since it seemed very easy to be promoted because at the lower levels they work every day. I'm sorry I didn't keep detailed records of the jobs Sims had. I wasn't expecting to win! When I started this family, Yesenia already had level 10 Fitness and Level 2 Fishing. Jaden had Cooking 1, Mischief 2, and Painting 3. While in this household, my Sim maxed piano, writing, violin, and logic and started working on handiness. He also maxed Mixology because he was making a lot of Prose and Pop and Amygdelight for the others. This couple had two children. I put everything they might conceivably need out on the lawn and locked them out of the skilling areas. I didn't want them talking to their parents becaus ethat would slow the parents' skilling speed down. They did come in handy when Jaden was working on Mischief.
Jaden: Painting, Logic, Piano, Charisma, Mischief, Writing
Yesenia: Fitness, Guitar, Logic, Fishing, Cooking, Gourmet Cooking
Family 2: Alice and Eric Spencer-Kim-Lewis
I deliberately delayed moving in with them until the elders died. I didn't want to deal with any deaths. Olivia aged up to a teen right after I moved in and she basically worked on Logic the whole time I was in that house. I wanted another Sim with maxed Logic I could invite over to help me mentor. Eric also had maxed Fitness when I moved in, which was quite lucky. My Sim continued to work on maxing skills, mentored, and mixed drinks. This house was pretty uneventful and straightforward.
Alice: Painting, Cooking, Gourmet Cooking, Logic, Writing, Piano
Eric: Fitness, Logic, Programming, Fishing, Mischief, Rocket Science
Family 3: BFF
More of the same. Liberty was my stay-at-home and it was here that I figured out how to get to Level 8 Gardening very quickly and without much effort. Liberty planted alternating rows of basil, strawberries, and snapdragons, about 50 plants in total. She watered them all after they were planted. My Sim watered them the second time they needed it. Shortly after that, they were ready to evolve. Then, she took cuttings and grafted until she got to level 8. This is where the alternating rows come in. Row 1: basil. Row 2: Strawberry. Take one cutting from the first two plants and then graft to the opposite plant. If you take multiple cuttings and try to graft the same plant, you will often lose the cuttings, so you have to do two plants at a time and just work down the row. I invited Yesenia, Eric, and Olivia over at various times to mentor.
Family 4: Pancakes
More of the same. Bob had a hard time leveling fishing and kind of slowed me down a bit. Neither of the Pancakes got a job. I found that as soon as Bob quit the Culinary career, the milestone checked off. Eliza maxed painting while waiting for Bob to finish up, so I now had another Sim who could mentor.
Family 5: McNamara
Journey(mother)
Blaire (YA daughter)
Javier (Ya son)
Same strategy here. Eric, Yesenia, Olivia, and Eliza helped mentor. Since I was getting short on time, I started using the socials for leveling Logic, Writing, and Painting. Basically, you talk about the skill twice
(discuss logic puzzles, enthuse about Iambic pentameter, and discuss color theory), do a random friendly interaction and do one more skill social. Then, cancel the conversation and start over. It's very tedious but if you do the same socials too frequently, Sims will become bored. It's much more efficient to use the socials, but I don't really have the patience for it. Also, I somehow only had 5 skills written down for Blaire and I didn't notice until I was close to the end. She worked very hard on the guitar skill, but came up 1/2 point short of Level 8.
Another thing I figured out during this challenge is that when you're trying to maintain an Inspired mood while writing or painting (I shake my fist at that pesky Confident moodlet!), don't let them finish the book or painting. Since this challenge was all about skill points and money didn't matter (Once I had bulldozed the houses, Sims had tons of money), I would just cancel the action when they got close to finishing the book or painting and have them start a new one. They were able to maintain their very inspired moods without interruption.
I didn't play the Goths because their ages were never optimal when I finished another family. I didn't want to deal with Mortimer dying and Alex's age was always an issue in my practice runs.
I went through a LOT of Prose and Pop and Amygdelight. This is something that I did that I'm not sure had an effect, but it's worth mentioning. When a Sim goes to work, select "work hard." After about an hour or so, change to "normal" and then immediately back to "work hard." Lather, rinse, repeat. When you switch from hard to normal, you'll often get a big jump in the performance bar. All of my Sims who had at least one job got promoted in 1 day. Is it any different than just selecting "work hard" and leaving it? I don't know. I haven't really tested it to see.
To level handiness quickly, I bought cheap toilets and tubs and had Sims do upgrades while my Sim mentored.
So, many thanks to Nutella and ClayMask for their detailed winning strategies. As I said, I borrowed heavily from both of them. Maybe next year I'll keep more detailed records, just in case!