Tip: Visit the acupuncture clinic in Soutenbori to gain skills Kiryu learned from Kiwami 1. You'll need to frequently visit the clinic from time to time upon completing substories.
The EASIEST way to earn money is by playing Nightlife Island (Four Shine) in Soutenbori. You can farm as much money as you want as long as you meet the requirements by your customers. Assign the right hostess to the right patron, you'll be all set!
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Game design difference #1. When you get to Chapter 4 in the original Yakuza 2, there are certain aspects of the chapter where you'll have to 'think outside the box' especially when you have to talk to the Mahjong Informant. Remember, always talk to Kurokawa (the purple suited thug that kisses up to Kiryu) so you won't have to pay a dime to the Informant when he asks for 300 grand:
In Kiwami 2 however, they've made it so that Kiryu realizes Esaki is hardballing him and decides to go to Kurokawa. In the original, you had the option to pay the guy 300 grand.
Game design difference #2
By far the most controversial at the time of its Japanese release, was the absence of Sinseicho - a third city featured in the original Yakuza 2. Sinseicho was based on Shinsekai and the
Tsutenkaku tower.
Pro-tip: Every week you'll receive Kiwami Fun Packs which contain characters for Majima New Clan Creator as well as costumes for Kiryu which you can swap in Premium Adventure Mode (complete the game on your first playthrough). It's easy to farm money in Clan Creator but you can farm millions in Nightlife Island.
Minor game design difference:
When Kiryu and Sayama enter the Millennium Tower to meet with The Florist of Sai, there is a cutscene in the original Yakuza 2 that was removed in Kiwami 2.
Gameplay scenario difference:
At the beginning of Chapter 7, Kiryu and Date take the injured Kazuki and Kawara to Emoto's Clinic. In Kiwami 2, you can make your way through the underground theater (inaccessible in the original Yakuza 2) to avoid pedestrians and police.
Game design difference:
In Chapter 10, Kiryu, Sayama and Date have a discussion about Bessho and Kawara. In the original Yakuza 2, the cutscene takes place at the docks where Kiryu fought against the Shimano Family where he learned the truth about his parents. In Kiwami 2, the cutscene takes place at the rooftops right above Serena.
Game design difference: In addition to Chapter 10, when Kiryu and Takashi meet they're both having a drink in Kiwami 2 but in the original Yakuza 2 they're awkwardly standing inside Shellac.
Game scenario difference:
During the sweet montage where Kiryu and Sayama spend some quality time together in Soutenbori, there's a scene in the montage in the original Yakuza 2 that's missing in Kiwami 2. In the original, Kiryu and Sayama are at the pachislots. Kiryu loses his chance at the slot machines but Sayama gets all Lucky 7's. This scene is missing in Kiwami 2.