Something I find mildly amusing is how some people fully believe Hisoka would HATE "boring" missions with Illumi. Missions where he just has to kill weak people and nothing else, even going as far as to threatening not to help him again if he doesn't up his game. I'm assuming this characterization comes from how he treats these types of missions with the phantom troupe. When he was told to go out there and go crazy in yorknew with killing the mafia, he just stood there enjoying the show but refusing to put any effort whatsoever to join in.
While yes, this is something he does with the troupe, its actually the complete opposite when it comes to missions with Illumi. In the election arc, Illumi asks him to get rid of hundreds of extremely weak hunters and he agrees without hesitation. Not only that, he's smiling all the way through, both on the phone and after spending his afternoon doing something everyone claims he hates doing. It goes as far as him placing a HEART saying they'll be busy when he agrees to fulfill Illumi's mission.
He's very clearly having fun. Which actually makes sense for his character, as Hisoka has been shown to enjoy the act of killing itself, even if its killing nenless people who are unable to defend themselves.
This was shown multiple times in the hunter exam, when he simply felt like killing other participants (even implied by menchi and satotz that he wanted to attack them too) because he was growing bored, killing participants in the fog all while laughing maniacally and having too much fun doing it.
Hisoka enjoys the act of killing, even resorting to it to calm his arousal down after thinking of fighting Leorio and Kurapika.
Then why would he just sit back and watch the troupe instead of joining in on the fun? How I see it, is that while he hates the troupe, he ESPECIALLY hates being told what to do. This is shown multiple times throughout the series, him constantly telling anyone who "orders" him to do something to pretty much fuck off lol (this post explains this further: here )
So why does he actually listen to Illumis orders? Very simple. Illumi is someone he respects and is the only person Hisoka considers a friend.
In return, Illumi also respects him. He doesn't mind following Illumi's orders, because Illumi views him as an equal, provides entertaining company no matter the mission, and has also followed Hisokas orders before (Yorknew, when he took disguised as Hisoka and took his place in the troupe as a favor.) While the troupe provided Hisoka NONE of the above. They all despise him. The feeling is mutual. Hisoka willingly cooperates with other people multiple times, but what makes cooperating with Illumi special is that he actually gains nothing from it, while other times with other people, theres always something in it for him.
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