Empire of Sin

This trophy is buggy, you fulfill the conditions, but the missions do not appear.
Perhaps my method is not 100% and it’s just a coincidence, but still. The first time I played, I did everything quickly, as with other bosses, and bought businesses through diplomacy, clearing the starting location of bandits and a “neutral” gang, and killed the bosses in the first location by ordering from other bosses (to do this, I first opened all card, immediately selected negotiations and agreed to the business agreement.
For the trophy we need missions in the middle mission slot. After completing the first such mission, the next one always appears after a while (about a game month). To avoid getting bored, I completed side missions and missions for the empire. As they advise on foreign forums, if you have judge “Ma” Miller on your team (and she is needed in the future to open a moneylender), then you do not need to carry out her missions. I did it, and in the mission, when Ruben calls to talk, I chose the dialogue option where I didn’t believe him and lied, giving a different address. After that, I didn’t get any more missions for the trophy, no matter how long I waited.
In the second playthrough, I killed everyone at the first location myself, but I didn’t touch the mission for the judge at all, and in a conversation with Ruben I answered honestly, giving the correct address.
In general, I recommend saving before each boss mission so that you can choose a different dialogue option if the game gets stuck.