This chapter begins again with a recap of the events so far in Kazuma Kiryu's story. Kiryu is joined by Nishikiyama at the battle cages, where he catches Nishikiyama up on the latest developments. Kiryu also reveals that he will plan on getting involved with real estate in the city. However, Kiryu must first set out to buy a business suit and asks for Nishikiyama's fashion advice. The two reach a shop in Nakamichi alley, where Kiryu eventually settles on the white suit that he will wear for the rest of the game. Nishikiyama laughs, stating that Kiryu does not look like a civilian regardless of what he wears.
Kiryu heads alone to Cafe Alps to meet Oda, who criticizes his clothing for being too flashy, a critique which he throws right back at Oda before he is given a pair of glasses to stand out less. At Cafe Alps, Oda begins to introduce him to some aspects of the real estate business. Oda walks Kiryu through a first business meeting with Yamanoi who is having issues with squatter named Tsuji. Oda sends Kiryu on a mission to get a confectioner's box to give to the squatter. In a confrontation with the squatter at the Sugita Building, Tsuji refuses to give into the demands of Tachibana Real Estate. Upon leaving the apartment, Kiryu is confronted with members of the yakuza who want to work with him, or at least pretend to, until he refuses the offer and fights them. Upon defeating the members of the yakuza, they reveal themselves to be of Hiroki Awano's Taihei Association, Tsuji agrees to vacate the premises and Oda directs Kiryu to a bar called Serena before parting ways.
After this, Kiryu need to go to Mach Bowl and make a solo report to Yamanoi. He passes by the Leisure King and his subordinate, who have just finished beating up Yamanoi in trying to make him close up shop. He helps Yamanoi reach the Sugita building, where he explains the situation in Shinjuku's Real Estate business and how the Five Billionaires are controlling it, before asking him to fight them. Yamanoi says he trusts Kiryu because of how he dealt with the squatter and because he's connected to Shintaro Kazama. At the office, he is introduced to the basics of running real estate and then asked to buy Sukiyaki Muranaka on Tenkaichi Street before he heads off to meet Oda.
At Serena, Kiryu meets the owner of the bar Reina and also has a reunion with his old friend Nishikiyama. They talk it over and sing karaoke to pass the time, wondering where Oda is and why he's so late. Eventually Oda makes it to the bar, but is severely beaten. He is quickly followed by Awano and other members of the Taihei Association. Awano tells them that Tachibana Real Estate has been causing problems with their business. The members of the Taihei Association respond by taking Kiryu outside in order to get a piece of him. After defeating his men, Awano questions his motives in being with Tachibana Real Estate and he believes that Captain Kazama is using Kiryu. Awano explains that he wants a meeting with Tachibana, saying Kiryu has until next morning to hand over Tachibana and clear his and Kazama's name.