@GlazeyLady That was ingenius. Congrats to you and the other players, too.
My approach was rather straightforward and primitive.
My Sim (acutely creatively called Hilarious Tormentor) had traits Loves the outdoors, goofbal and family oriented, plus quick learner bonus trait. I moved him to Windenburg next to Partihaus household. Just when he got to the game, he switched to Fab. wealthy aspiration to get some instant points, and also cycled through some other aspirations. I built him an uber basic place, mostly outdoors, no cooker, just a fridge, etc. Lot traits: convivial, great acoustics.
He watched clouds and played the guitar for a while until the Partihaus members came for welcome wagon, which I used to get rid of the first tiers of both Chief of mischief and Joke star aspirations. I only used funny socials on Sims that I did not want to make enemies with, plus occasional Brag about family (hence the family oriented trait), as it raises the friendship quickly, and I wanted Hilarious to make at least one friend. Then he mainly worked on the mischief aspiration as quickly as possible. I tried to keep him at home amap (because of the lot traits). For clogging the drains, he went to all three community lots in the Old Town (literally one click apart) and did it there, as it counts if you do it on the community lot, too. My goal was to get 3000 points asap, spending 400 in the process for a sleep replacement, but by Monday morning there was enough to buy Connections. At that point Hilarious dropped whatever he was currently doing and then entered and quit all the careers except for the entertainer, which he joined at the end. I sold all the career rewards except for the ones giving playful or inspiring aura, and I also kept some powerful happy decor. Hilarious then had enough money to not only buy the Wishing well, but to also make a few 5000 offerings and wish for a promotion while in a great mood and having had fulfilled all the criteria for promotion to level 5 of the entertainer career (he needed to up the guitar skill first). At the first wish, he only got a meh answer. The problem was there was less than 8 hours until the start of the work shift at that point (8 hours is the well's cooldown), so Hilarious took a vacation day and worked on his skills instead. As soon as it was possible again, he made another offering and wished for a promotion again, this time being promised a promotion by the end of the shift. He got promoted within a few hours, at the end of the shift which he took a vacation day for, so he ended up not going to work at all. I think I had him quit after he chose the comedian branch.
For his needs, he used sleep replacements and instant hygiene, and he was constantly munching on ham sandwiches while socializing.
The rest was pretty much just about skilling. I am not sure how the Confident emotion plays into social skills, but I used solely Playful for both mischief and comedy, or actually, Very Playful. Very Playful is between +8 (counted across playful+happy moodlets) and +14, Hysterical starts at +15 I think, so my goal was to aim at +8 something. For this, I used playful decor from criminal career, and then just funny interactions to get in the mood; telling many many jokes in a row gives a few powerful longlasting playful moodlets that stack. Plus Hilarious had LTO and goofball traits, and I also had a few pieces of just happy boosting decor with varying strength in the household inventory, so that I could place various combinations of those on the lot to tune his mood instantly (for example, when he was on the verge of hysterical, I took away a high value statue and disabled emotional aura of something else, etc).
For leveling mischief, he used only socials (apart from fulfilling objectives of the aspiration), but he avoided tricking with hand buzzer (risk of Dazed). Once he was at lvl 5 mischief, he bought several voodoo dolls and bound them to several Sims, including the only friend he had made, not only so that he could summon Sims to interact with instantly, but also because from that point, he only built mischief by doing voodoo. From my testing, the effectivness of various ways of building mischief was as follows (from the weakest): skill book, trolling teh forums (spam money request does nothing for leveling), regular mischievious socials, voodoo. Socializing gives +4% skill raise per interaction (while very playful), whereas voodoo only gives +3% per interaction, but voodoo interactions are much shorter and it is overally faster (even if it backfires, it only gives a weak uncomfortable moodlet, and if it backfires again before the moodlet expires, it does not stack, just resets the timer). The only caveat: he only could use poke, soak and tickle, as the other two raise charisma instead.
For leveling comedy, again, he used only socials. Here, the order was (from the slowest way to build the skill): writing jokes, skill book (with Peace and quiet lot trait), telling jokes at the mic, socializing. Then, within the socializing, regular jokes give +3% skill raise per interaction (while very playful), funny story gives only +2%, but making funny faces, which is only available among friends (at least I believe so) gives +4% and is quick. This is why I wanted Hilarious to have a friend and tie them to the voodoo doll, so that he had a stable victim to make funny faces at 3648 times in a row (his friend ended up to be Nancy Landgraab, and she actually seemed like she was having tremendous fun; the interaction tone was "hilarious reparte," something like that; they became friends solely via funny socials and occasional brag about family).
All in all, the cap in this challenge was the skilling. A very very good idea to make us do this without clubbing, I enjoyed it thoroughly.
