Empire of Sin

Introduction
As of writing this guide the game is very simple to complete but may change in future patches.

All of the achievements can be done in any difficulty level.

This guide was written for PC Version 1.02. Other platforms is unknown to me but should be similar.
The Run Down Redigera
Your first game will be the long game. This will get you introduced to the game mechanics and learn the tricks on how to make it fast on the busy streets of chicago. At firsy you need to have some time to practice how combat works. Specifically how full and half covers work, weapon range and effectiveness and rarity color. Some minor things such as thugs not using grenades but AI major faction mobsters do. Teaching you these things do not fall under the scope of this guide but are things you will learn keeping your eyes open while you play. Remember to save frequently because of bugs and if you accidentaly get a mobster killed if you are running for the bulletproof achievement.

You will be knocking these achievements out in your first game:

Jack of All Trades, Master of None
Own five of each racket type

There Goes the Neighborhood
Took over a neighborhood

Public Enemy 1
Became Enemy of the State while maintaining the highest notoriety

Maximizer
Get a hotel and have all synergies simultaneously

Bulletproof
Finish the game without getting anyone in your crew killed

Bullseye
Take down all of an enemy's health with a single shot

Let This Be A Warning
Perform an execution

Trust Me
Land a hit with 10% or lower odds

I've Got Your Back
Form a Business Arrangement

I know A Guy

Reliable
Max the loyaltyt of one member of your crew

This Never Happened
Bribe a cop

I'll Be Back
Have someone in your crew go to jail

My Specialty
Get a synergy bonus

On My Own
Complete the tutorial

Your middle games will be focusing on winning as each of the mobsters. The strategy for doing that is the same for each one of them and is fast and efficient but repetative and boring.

Your last game will be the lone wolf achievement. This is where you win the game without hiring any mobsters.
Your First Game Redigera
Starting off select your favorite mobster that you want to do a longer playthrough with. Set up the game with the biggest map with the most AI players. Difficulty is your choice. I've tried all of them and one difference I found was the AI used less explosives on easiest difficulty. You start with more cash on easiest but the AI can still attack you.

Your first achievement starts with going through the tutorial. Go through tutorial and when you have downed the boss perform the special "execute" ability on any of your gangsters.
Remember to save the game frequently and especially before each fight. If you lose a gangster you miss an achievement.
Do sit downs with any mobs you come across and try to make deals with them. At first you want good relationships with as many as possible. Agreeing with their trade offer will grant you "I've got your back" achievement.
Reveal all hidden areas of each neighbourhood while looting all crates you come across, guarded by thugs.
Trade all green items for AI's money, purple items, healing items, explosives, armor, and low tier alcohol.
When your can't carry any more alochol trade the cheap stuff and disguise it as expensive alcohol back to whoever has any money left that does not like you very much.
Build up your noteriety by attacking free buildings, AI minor factions, or any major AI factions that have declared war on you. You can also declare war on an AI that dislike you very much and won't trade with you.
Get a crew of 5-6 mobsters (you included), equip everyone with the highest tier weapon they can use. 1 explosive and one healing kit. Put armor on them and then attack a major AI faction's safe house.
Position your crew apart from each other so that if the AI throws an explosive it does not hit many of you.
Aim to take down a hired gun. If a hired gun dies most other mobs will panic and they will move to the exit. This will give you 1-2 turns of free moving around/shooting. If the enemy boss is nearby aim to take him out because it will have the same effect in additon to giving you the opportunity to escape with your crew without killing the rest and still defeat the AI and get all their territory.
Remember to save the game frequently and especially before each fight. If you lose a gangster you miss an achievement.
As your income grows and you got cash on hand, consider bribing the police and see if you can become their friend. This will open up their shop and you might be able to get some good explosives, armor or weapons.
Try to knock out as many AI as you can like this except one. You want 1 to survive so that you can work on your other achievements. Keep recruiting gangsters as your noteriety goes up and remember to beef them up with gear from the black market, or police.
Once you are down to 1 boss, preferably with only their safe house left, focus on the other achievements. By defeating most AI you should have knocked down "Jack of all trades", "there goes the neighbourhood" (if not simply attack free buildings in the same neighbourhood until you have most of it under your control), "Maximzer" and "My specialty".
Now go to the police faction's window and bribe them to get "This Never Happened" achievement.
Hire 1 mobster from each category to earn "I know a guy".
Equip as many gangsters as you can with shotguns and take those guys and hit free buildings. Your aim is to get in a position where you can hit a target when the chance is 10% or lower. Just keep trying it will happen eventually.
For the Bullseye achievement. If you have not gotten this already take all those that has the ability to use a sniper rifle and equip the highest tier you can and then go to free buildings and position yourself far away from the target and blast those whom you can or close to can one shot. If it says you are close to 1-hitting do it anyway because if it crits you might be able to hit. Rifles and sniper rifles work best.
"Reliable" is done by having a mobster's loyalty get to max. If you open the window of one of your mobsters there is a menu where you can see what has given loyalty to that person in the past. Just do those things until you get the achievement.
" I'll be back" achievement can be done by taking 1 of your crew and attacking the police. Save before you do this. Let the police get their health down and hopefully they will arrest you. You want to attack the police away from your buildings because you don't want any guards to help you out. You want to be arrrested and the combat to be over. Once you got the achievement. Reload your previous save before you attacked the police because I am not sure if an arrest counts as one of your crew getting killed.
At this point if your noteriety is not maxed out just keep fighting thugs in buildings and taking them over. Do quests or kill cops. Killing cops will make some of your crew lose loyalty.
Once your noteriety is maxed just kill a police officer and you will get the achievement "Public enemy nr 1"

Now you will hopefully have gotten a whole bunch of achievements. The rest of the "kill x boss" achievements can be done while trying for the rest of the achievements. If you are very unlucky however and do not get a chance, simply keep doing games until you get a kill of the required boss.
Your Middle Games (amount depends on luck) Redigera
These sessions will solely be to win as each of the bosses in a fast and reliable way.

The first step is to make a small map with least amount of mobsters for quickness. The first step is the same as in your first game. Go around the map and pick up crates, do sit down with bosses, and take all their money, their unique weapon, explosives and healing kits in trade. Take their booze and sell them back as higher tier for good money. The one person you do not want to screw over is the one that starts with highest relationship with you. This is our puppet.

The current patch allows us to spam the assassinate request button multiple times. Simply go to the boss that has the highest relationship with you and spam request a hit on all other bosses. Each hit has a high chance of failing so the more times you request a hit on the same boss the higher the chance you will eventually get him wacked.

Once you are down to 1 boss (he will own the entire city by now while you are still small) equipt your crew with the best gear, declare war and hit his safehouse. Eventhough he owns most of the town he will be just as easy as he was in the beginning.

Keep doing this for every boss you have not win with yet.

If you have the option to chose which boss that is going to attempt to assassinate the others, opt for the boss you have yet got the achievement for killing, that way you can hit two birds with 1 stone.
Your Last Game (Hopefully) - The Lone Wolf Redigera
This is by far the most intimidating achievement to get. But with just a little bit of belief in yourself and either luck, skill or reloads, you can easily get it.

The Lone Wolf is the achievement where you need to win the game without recruiting any crew. That means no tutorial crew, no nothing. Just your lone self fighting the other mob bosses.

To make things easier take a boss with a good boss ability. St. Claire would be a poor choice in this regard but OBanion would be excellent. O'Banion has the ability to fire an explosive shot which will destroy the enemies armor and damage them. For best effect wait until you got all of his skills but it is not necessary. Equip a machine gun and explosives and healing. Optionally the flask that gives movement speed/health.

For ease and quickness, use the smallest map and the least bosses. Run around and pick up crates. The aim for the crates and trades this time is simply to get good armor, explosives and a good gun.

Use the request a hit strat mentioned before to have 1 mob get rid of the others. This way you won't actually have to defeat the other mobsters yourself, just 1 of them. If you were to fight the others as well you run into the problem of not having enough explosives or good armor to defeat the last one.

Here is where luck may play a role. For each generated game each boss will have one of several boss room maps. If you are lucky you can get a map where the boss spawns right next to the entrance and so you just need to run over there and kill him. I was not lucky but made it work anyway.

The reason this achievement is easier than it seems at first is because you don't have to kill everyone in the room to win the game. You just have to kill the boss. You can either get killed yourself or escape the room after killing the boss and you win.

You want to try to get to the boss asap and isolating him/her if you can. If you are on the map where the boss is on the very other end of the entrance and the room is split by a long wall with two entrances one at the top and one at the bottom: go to the end of the wall seperating the room and wait for the non-boss mobsters to run downwards so that they are at least half way down the room. Then run up towards the boss and you should have enough time to kill him/her before the rest can come to the boss' aid. Remember grenades destroy armor and do good damage.