Ok, I have something to say. This may be controversial to some writers, but whatever.
I don't think Chrollo, Yandere or not, would ever get the troupe to watch after or steal something for his s/o. If his s/o was maybe in like a life or death situation, he would probably, but not much other than that. Chrollo loves his troupe very much. They're his family, friends, his people. The spider is his dream, and the members in it are so, so important to him. Chrollo and Yan! Chrollo alike wouldn't just boss around and abuse his powers as the Phantom Troupe leader. He only really commands them when it's troupe related, like for a mission. Other than that, they can do what they want, and he and the entire troupe knows this.
Now, even if he DID tell/ask them to, would they keep an eye on his s/o, or steal something for them? yes, they would. The troupe loves chrollo just as much as he loves them. But the thing is, from the very formation of the troupe, he was chosen to be the leader because they all knew he would be a good leader. And part of being a good leader is not abusing your power for your own personal life.
I feel like another exception I could see is if his s/o is friends with a troupe member.
I know, I love the idea of Yan! Chrollo constantly keeping tabs and an extra pair of eyes his s/o, but I don't think he'd get them to do it. First off, I think he'd like to keep his romantic life seperate from his work life until he has had his s/o for a little, then he'll introduce them. Secondly, I don't think he would want an extra pair of eyes on his darling. Because that's his territory.
Anyways, moral of the story, regular Chrollo and Yan!Chrollo wouldn't send the troupe to do tasks like spy on his s/o or steal something for them. You guys can think otherwise, but I won't. I will stand and die on this hill.
