Empire of Sin

Works with all bosses. This is just for anyone who wants to finish winning with the specific boss achievements.

When starting I always Equip the gold shotgun that's free (if you have the deluxe edition) or any decent gun, recruit Judge Ma Miller (requires make it count dlc to get the loan shark, which you have to talk to her to unlock when her mission becomes available) and upgrade all the rackets you start with as much as you can with your starting money. While they are upgrading I go through all the neighborhoods looking for the brown dots, these are thugs and they all have chests by them (not required but useful items like body armor and other items for improving relationships or getting money through trading). I zoom in when near them and press B and shoot one that I'm standing right next to, this gives you a free kill before combat starts, then I kill the remaining ones. Rinse and repeat through all the neighborhoods.

As I meet new bosses I request a sitdown, I do not attend the sitdown until I get the notification from them that's says they are waiting and it is going to time out, at that point I will then fast travel to sit down. I always negotiate the proposed business deal and ask them for 10% of whatever money they have (say they have $5,421, ill ask for $542. They almost always agree) and I continue doing this until I've cleared all the thugs and met all gangs and attended all sitdowns while upgrading my rackets when they are ready.

If you have gangs in your starting neighborhood then ask gangs that are friendly with you to kill the rival gang bosses. When you kill a boss all the rackets are vacant and you only have to take over the precinct safe house you have access to build whatever you want. Once you get the notification that a gangster is making a move to kill a boss then save right away, they will tell you if they succeeded after a couple of minutes. If they fail then just reload that save. It may take several reloads for them to be successful, but it seems random as after reloading I do get successful attempts

The first large buildings I get I build breweries and upgrade production and quality. I always make sure my production and quality is upgrading at my breweries, you want those maxed out. You can see your alcohol information by clicking in right Stick and hovering over alcohol icon at top of screen. I build at least 1 of every racket in each precint

Offer protection deals to anyone that you can, whenever gangs ask to buy alchohol, accept. I usually use 2 or 3 bosses to kill the other bosses while i have active bussiness agreements with them. I have them kill bosses in my starting neighborhood and the ones that I have low relationship status with. I always take over my starting neighborhood and fill with rackets, upgrading them as i go. I'll typically stretch a bit into neighboring neighborhoods. If gangs in your neighborhood are expanding into other precints that's good for you becuase once you have a boss kill that boss then that's less thug rackets you would have to clear out.

Continue the process of eliminating bosses and upgrading rackets until there is 1 boss left and I'm making about 50k a week. You have 2 options once there is one boss left. Buy them out (requires 300 freindly relations and 3 months of having procted them) or hire gangsters until you have 10 to attack thier safe house and eliminate them, you need to find thier main safe house first though, and you cannot be actively protecting them in order to declare war. If you want to buy them out (like I usually do since I end up in long protection treaties), but you don't have a good enough relationship with them, then you can trade with them. Give them stuff for $1 to get maximum impact. When you take out the thugs you have a lot of things to either sell or trade to improve relationships with any boss at any time. You can give them items or any type of alchohol. They do have an alcohol storage limit though that you can see on their diplomacy page so don't just give then a bunch of your low quality stuff as it won't improve relationship as much as a higher quality

I suggest doing the cop bar mission (appears on the street map of random neighborhood). You will get good relations with the cops if you let them use one of your bars and I've only ever lost a little bit of respect from one of the other gangs from it, which you can easily get back if you need by trading. DO NOT POISON the cop bar when it asks you later on. By doing this mission the cops seem to be more relaxed with you. I Also try to make sure my precinct heat stays below 50 or so, if it's getting high I start only upgrading deflect and building in a precint with lower heat for a while. Mob lawyer helps with this also which you can build after upgrading that precinct safe house to a high enough level

For anybody who is interested in the results from the Journalist interview mission that is found in the streets, its called getting personal with Chicago's underworld

First question
Two screwdrivers= +1 Melee
It was an accident= +1 Marksmanship
Dealing in hooch= +1 Initiative

Second question
Not long= +1 Persuasion
Ten years= +1 Intimidation
I busted out= +1 Leadership

Third question
Robbing hooch= +1 Intimidation
Taking over Chicago= +1 Leadership
Radio star= +1 Persuasion

Fourth question
Live large= +1 Marksman
Why give advice to future rivals= +1 Defense
Follow your dreams= +1 Melee