I'm running into the exact same issue.Greetings, I can't activate this task in any way, I've already tried everything.(I came on weekends, during the day, at night), I even thought maybe it was necessary to bring some girls to the end, it didn't help either, maybe who knows? It turns out that it started after the "introductory" missions with the triads View attachment 5003293
It seems like there's supposed to be a trigger after you are done previewing all the gangs but nothing happens.
Attaching a save incase it's mod related but i get the feelings it's a me missing the obvious path situation that often causes this game to stall.