My overall strategy was two-fold: add the townies to the household that were closest to completing the longer tasks and micromanage like crazy.
The first part was a "set up" to get the right sims in the household and complete the rosebud achievement. My starting sim (named Number 24) was a spellcaster who had the traits 1) bookworm, 2) materialistic, 3) animal lover. The first two were so I could screen out townies for my club, and the last was so this sim could befriend 4 animals faster. I moved in Number 24 to bargain bend, made it a tiny home, and created club with the following sims who would also join my household, Darrel Charm (bookworm), Yasmin Tinker (bookworm), Thomas Watson (materialistic), Judith Ward (materialistic). Number 24 then befriended them. At various points, I swapped in Eric Lewis, a landgraab, and Jacques Villarel into the club and befriended them as well. I then moved in Darrel, Yasmin, Thomas, Judith (plus Gemma Ward and Maira Watson, who both start with B grades in school). I also moved the combined the household with the Lewis/Langraab/Villarel lots in sucession to add their money the household income (for the Rosebud milestone). Along the way, one of the sims met Ekram Elderberry, and he was swapped in for Maira Watson (I'll described more below). The final person added was Judith Ward, because her house is 3 windows away from the mansion baron aspiration, so once I added in those windows, everyone in the household got a good chunk of aspiration points to purchase traits to assist in their respective tasks. Finally, the household was moved to the vacant lot in the vampire world, again which was made a tiny home residential. In all, this took roughly 4-6 sim hours.
The second part was doing the tasks. I'll describe them in the rough order finished:
1. Have 200K (finished in set up)
2. Acquire 1000 SM followers (Judith streaming with a drone - she gets 250 per notification)
3. Earn 3 career rewards (Darrel bought connections and cycled through a couple jobs to get 3 career rewards)
4. Get married (Darrel invited over Emilia Ernst, whom he's engaged to, and got married)
5. Woohoo in four locations (Darrel woohooed with Emilia Ernst in four different locations - bed, closet, shower, and tent)
6. Emotional sculptures (Gemma leveled up handiness to level 2, and used flirty + playful lamps to get those sculptures + Number 24 cast the despairo charm to make her sad. Thomas, who was a hot head, made the angry sculpture, after being riled up by Darrell, getting the hothead angry moodlet, and setting an angry vibe to the club)
7. Repair + Upgrade an item (Darrel broke a toilet with zipzap, and Gemma repaired and upgraded it)
8. Befriend 2 occult (Number 24 befriended Darrel + Caleb Vatore, who swung by since the household lived in Forgotten Hollow)
9. Befriend 4 unique animals (Number 24 befriended a llama, cow, chicken, and a rat)
10. Spend 10 hours exercising (Tomas spent the bulk of the first day accomplishing this)
11. Paint a masterpiece (Judith bought the creative visionary reward trait, home lot was set to home studio + natural light, she leveled up her painting skill and eventually painted a masterpiece using the virtual easel which is faster than the regular easel)
12. Have a toddler get to level 3 in all skills (immediately after moving to the vampire world, Number 24 adopted a toddler, Eve, and hired a nanny, who helped Eve level up all skills. Thinking -> "watch" action, potty -> potty, movement -> "play" action, imagination -> toddler tent, communication -> bear stuffed animal)
13. Catch a rare fish (Ekram, who started at level 8 fishing, caught a vampire squid in one of the fishing spots in the vampire world)
14. Write a bestseller (Yasmin, who started at level 8 writing, purchased the creative visionary reward trait. While the lot trait was set to home studio and she was very inspired, she wrote only children's books. On the second attempt, the book was a bestseller)
15. Make 10 Unique Excellent Meals (Once Darrell + Thomas were finished with their first tasks, they both cooked in separate kitchens, (with locked doors, so they didn't try to use each other's stoves). Not that it really matters, but the excellent dishes they made were: Grilled cheese, eggs & toast, Faux BLT, Mac & Cheese, Garden Salad, Minced noodles, Paleek Paneer, Butternut Gnocchi, Garlic Noodles, Fruit and Yogurt Parfait
16. Max two different skills (I had to max multiple to get 500 Achievement points, below, but the first two were writing (Yasmin) and cooking (Thomas)
17. Graft a plant (The first thing Thomas did was plant some fast growing plants for the grafting. Since i set the season to summer, he planted green beans. Thomas starts at level 5 gardening, so he was able to take a shoot once there was a mature plant in the area, and it was only a matter of waiting for the green beans to reach maturity)
18. Purchase at least 24 unique perks (As soon as Judith painted her masterpiece, she booked a celebrity cleanse, which reset her 10 fame points, which were used to buy 10 fame perks. Number 24 had acquired 1 spellcaster perk point from trying to learn despairo, and I had the other sims create separate clubs so they could buy different 100 point club perks, which is the default amount of points that a new club starts with. In total there are 15 or 16 of these, so I got enough so that I had 24 across these three sources)
19. Have two different school-aged children get an A (Maira, as soon as she was moved in, made a wish in the Wishing Well for better grades, and out of pure luck got her wish granted on the first try. Once this happened, I moved her into the Spencer/Kim household in the setup phase, freeing up a slot for Ekram. Gemma also wished 3 times for better grades in the Wishing Well (8 hr cooldown), but was unsuccessful each time. To complete this task, I had to move in Darleen Walsh (after Judith came back from her celebrity cleanse). Darleen also starts with a B, and luckily, she got her wish granted on the first try. I did learn in this process that Rohan Elderberry starts with an A . . . so this was not the most efficient method of completing this task)
20. Throw a gold medal party (I intentionally held off on this one because I didn't want the +3 confident moodlet for the household. Number 24 had a great reputation by this point. She held a dinner party, where using one of the meals Thomas/Darrel cooked, called everyone to eat, which boosted the party into gold)
21. Steal an item worth $1000 (The first thing Darrel did was teach himself Burgulariate, since he's the only in-game spellcaster at the right level to learn that spell. This took some time, but he comes with the perks to speed up the experimentation process. He traveled to the museum in Selvadora and stole the golden omicasan plate on display)
22. Acquire two unique items from vacation (The first item was the gold plate, above. The second item was an insect that Darrel burgulariated from the nature house in the national park in Granite Falls)
23. Find six different types of collectibles (found more than six here, but when sims had spare capacity, they went search for collectibles and found: a frog, a mysims trophy, a plant, a fish, the holiday crack plushie + the insect / omicasan treasure from the vacation worlds)
24. Rank up at least 500 Achievement points (This was the slowest to complete. I completed Rosebud, the most interesting sim in the world, some of the easy 10 pointers (e.g., bladder failure on a date and with 5+ toilets). The other points came from the household trying to level up a skill to level 10 - writing (Yasmin), cooking (Thomas), gourmet cooking (Darrel), Fishing (Ekram), photography (Number 24), charisma (number 24), comedy (Thomas)