The Winery Boss, but in Yokohama

[Provisional Blurb] One day, Kaito Karasuma obtains a full-dive game called The Boss Simulator. Although the description is long, it boils down to this: as the heir to an international criminal syndicate, he has to manage the family business successfully while dealing with threats from both within and without. But after looking over the character stats of his own organization’s members, Kaito Karasuma falls into a long, profound silence. Why are they all either fake booze or watered-down liquor? The one genuine bottle who seems halfway decent is always taking out his own people. Seriously, how is he supposed to beat the game with a starting situation like this? As he wonders about that, Kaito Karasuma turns his attention to the Port Mafia, a potential ally in the neighboring Yokohama region. Looking at two characters with excellent stats across the board, Kaito Karasuma has a stroke of genius. Managing the family business himself is no match for stealing someone else’s best subordinates and then kicking back as a hands-off boss! When he tells his subordinate, Vermouth, about his idea, she visibly chokes up a little. “...How is this any different from retiring as soon as you find a partner?” At that moment, Kaito Karasuma sees the light. He feels he has invented a new way to beat the game, and finally understands what people mean when they say that unorthodox cultivation gets results fast. (Not really.) * Sneaking into the Port Mafia, Kaito Karasuma gets to work recruiting people (no) finding a partner (yes). For the black-haired young man, he gifts him bandages and cooks crab dishes... For the auburn-haired young man, he gives him fine liquor and learns all about motorcycles... [System: Dazai Osamu's affection +1.] [System: Nakahara Chuuya's affection +5.] Raising both their affection levels at the same time is risky, but the payoff if he succeeds is truly worth it! That is what Kaito Karasuma thinks as he watches their affection bars steadily rise, until one day the two discover each other’s existence, bringing his plan to an unavoidable end. Kaito Karasuma: ... Kaito Karasuma: Looks like my plan to find a partner and retire has failed. In that case, let’s part on good terms, haha... ** Recently, Mori Ougai has noticed a strange atmosphere between two of his subordinates. After hearing the rumors going around, he calls them both in to question them and learns what happened. Mori Ougai: subway, old man, phone.jpg But when he pieces together from their story that Kaito Karasuma is the new leader of an extremely wealthy (the important part) international criminal syndicate, Mori Ougai presses his hands together beneath his chin and falls into thought. After a long while, he looks up at the two subordinates in front of him and cautiously asks: “Since the organization hasn’t suffered any losses, if it comes to it... could one of you make a sacrifice and go along with him?” After all, nobody turns down money. Mori Ougai questions it, understands it, then surpasses it. The two of them: “...???” Is that really something a boss should say? By the time Kaito Karasuma returns to his own territory, he has already decided that as long as he stays away from Yokohama, he won’t have to worry about running into those two again. But he never expects to encounter them the very next moment, at a joint business meeting. The two sit across from each other, but the unusual atmosphere makes them stand out in the entire venue. Perhaps sensing his arrival, they both turn toward the entrance almost at the same time and stare intently at him. At that moment, even without a notification from the System, Kaito Karasuma knows what they are thinking. [, Finally, we’ve got you.] [Reader's Note] ▲ Retiring after marriage: A concept specific to Japanese society, referring to leaving the workforce after getting married to become a full-time housewife or househusband. ▲ An atypical Fourth Calamity, with a poly relationship between Double Black and Kaito Karasuma. ▲ More to be added if anything comes to mind. Theme: Stay positive.