This challenge is now closed.
Congratulations to Nikitachi on the win. Everyone is now free to discuss strategy.
Thank you!!!
There's not that much strategy here, actually. Before I started, I made one test run where I allowed myself to cancel whims - just to make a list of them - and I ended up finding 147 in total.
Now onto the sim. First of all, I chose him to be a Vampire. Why? Because a Grand Master Vampire can use a power named 'Influence Emotion' which allows your Sim to give an emotion to nearby Sims. At rank 3, it gives +8 versions of emotional Moodlets which is in most cases enough to make a sim get the required mood.
Also, I made sure not to choose any traits that can randomly give a 'good' moodlet (like happy, focused, etc.). Instead, I chose Snob, Hates Children and Kleptomaniac. When the game started, my vampire instantly became bored because of an unattractive environment - so I quickly completed a lot of Bored-related whims. Then I proceeded to other 'bad' moods. For Angry, I used an Angry bear hat and the Angry club aura. For Sad, I used a Sad Panda hat and a Sad club aura as well. For Dazed, I drank a lot of coffee. For Embarrassed, I used the 'Celebrity Home' lot trait or tried to steal something when having other sims in the room. Tense moodlets appeared on their own because my sim wasn't working on his Fun need. When new moodlets within one mood stopped appearing (or there was one I couldn't complete), I switched to another mood, and so on.
Only after completing most of the 'bad' moodlets from my list, I started working on Happy moodlets, and then - on all the other emotions left. If I didn't do them in this order, good moodlets would outperform the bad ones, and I just wouldn't have been able to get into any of the bad moods.
Meanwhile I was also slowly but steadily raising my Vampire's rank by using 'Detect Personality' and 'Cast Hallucination'. When he became Grand Master, I invited 7 sims to join my household and then made them getting all the required moods in just a few sim minutes.
