He saddles one of his guards with running the village. She watches him do paperwork often enough, and is one of the few who came out of Orochimaru's regime without anyone holding strong grudges against her. She is not particularly impressed.
Finding someone else to make sure Itachi neither starves nor escapes is a bit more of a pain, since he's taking Karin with him. Possibly illicit or at least hypocritically held captives are a headache, who knew. Still, Karin has those she recommends, primarily healers with enough discretion and loose enough morals. Which is all of them except the trainees and a tiny handful of recent arrivals. He picks someone with the talent to simply keep his sister unconscious safely, and then turns his attention to making sure no one sets his village on fire while he's gone.
He will be sorely disappointed if they can't survive a few days without him, but life is full of disappointments.
Still, Sasuke's ready for Ellisaria outside the main entrance, Karin and Juugo with him.
He nods to Ellisaria when she arrives, and says, "This is Karin, and this is Juugo. Juugo is strong, but has a condition reducing his ability to consistently control his actions, which I can keep in check better than our other available options, so I made the call to bring him." And taking Juugo gets the captain of his guard slightly less annoyed with him over this.