A conversion of the 1e Oriental Adventures yakuza. Not 100% happy with it, but it works.
YAKUZA
The yakuza is many different things, depending on who is asked. He has been called a protector of the common man, thug, extortionist, rowdy, thief, mercenary, jack-of-all-trades, and even an unofficial police force. He is simultaneously despised and respected, sometimes even supported by the local daimyo. On one hand, he represents the shadowy underworld, directing and controlling illegal activities. On the other hand, he provides protection for the helpless and watches over those under his care. Of course, such paternal care has a price, and it is from this that the yakuza makes his living. Because the powers of a yakuza come from dealing with other people, the character class is only truly effective in urban areas. Yakuza operating in the countryside find their life lonely and difficult.
Persuasive
3rd-level Yakuza feature
To be successful, the yakuza quickly learns to master the art of dealing with others. You have advantage on Charisma ability checks as well as related skill checks.
The Family
3rd-level Yakuza feature
The family of a yakuza is not your natural family. Upon becoming a yakuza, you are adopted into a yakuza kumi or organisation of yakuzas. This arrangement is identical to a normal family clan. There is a family head (oyabun), uncles, fathers, and brothers. You are expected to treat these members as if they were blood relations, and indeed some of them may be related. The yakuza family does have honor (Zingl) which must be maintained. Belonging to the yakuza family does have its rewards. Your living expenses and those of your friends and associates are automatically covered by your monthly stipend.
Information Broker
3rd-level Yakuza feature
You are an information broker and can dig up all sorts of useful information through discreet inquiries – gain the floorplans of a residence, learn where a lord conceals a particular item, obtain the guards’ schedule at a daimyo’s palace, learn who stole a particular item, obtain the identity of a police informer, find a shady merchant willing to buy stolen goods, etc. You become proficient in Investigation, if already proficient, you double your bonus.
Faceless
3rd-, 9th- and 13th-level Bushi feature
You may choose a class feature from another roguish archetype. It must be a feature of the same level or lower than the yakuza class feature.
Contacts
9th-level Yakuza feature
Another resource of the yakuza is his contacts. Contacts are NPCs who can provide you with specialised information and aid. They will not join you on adventures but will buy stolen goods, provide a secure hideout, carry messages, and provide information. Contacts never do anything that might put them in peril, although they may risk their reputations. They remain cooperative with the yakuza and silent about his activities (and their involvement) so long as they are fairly treated, not threatened, and not implicated in anything. A yakuza character receives one contact for every two experience levels. A contact can also allow you to more easily buy and sell magic items.
Ki Step
13th-level Yakuza feature
By focusing your energy you can sense and anticipate your opponents’ moves for short periods of time. This lets you position yourself to minimise the danger from an attack — sidestepping slightly at the last minute, partially blocking the target point, etc. This ki power does not foil the attack, it only reduces the amount of damage the character suffers by one-half (round fractions up). The power can be used once per short rest.
Tats
17th-level Yakuza feature
Your tattoo takes on magical properties. You may select a tattoo from the list of the tattoed monks and your yakuza tattoo now has that magical effect.