To earn this achievement you must complete all levels of all activites available in Stilwater. Below is a list of the activities and a good method of completing them. All activities have three locations with the exception of Demolition Derby, which appears once, and Snatch, which appears four times. There are eight levels that need to be completed at each location. Also, Loan Shark does not need to be completed in order to obtain this achievement. You do not need to find and spray all tags either.
Hitman- For this activity you will be given a list of enemies that you must kill with a certain weapon. You can also add the targets to your HUD, and a crosshair icon will appear on your mini-map when they are near.
Chop Shop- This activity is very similar to 'Hitman.' You will be given a list of cars that you must steal and return to a garage. Again you get to add specific cars to your HUD, and a yellow car icon will show any in your area.
Racing- The racing activity is very simple in this game. You must beat other cars to the finish line. Sometimes you will have a multi-lap race, other times you will have to race from one checkpoint to the other. To easily win, instead of using a sports car like the Attrazione, grab a police FBI SUV. The game will match you up against similar cars that won't be able to match the superior handling and speed of the FBI.
Demolition Derby- To win this activity you need to blow up other racers and cause damage. The best way would be to use nitrous (RS) to build up more momentum for a greater impact. Also attempt to ram cars that are already damaged badly.
Insurance Fraud- You are supposed to throw yourself in front of vehicles to earn money in this activity. However hitting the trigger will only bring in a couple hundred dollars at a time, if you're lucky. Instead, acquire a police cruiser and drive to the target area. Try to get as close to the blue square on your mini map as possible. Make sure you are on a long, straight road though. Now floor your car and collide with other drivers head on. You should fly through the front windshield and land somewhere down the street. If more oncoming cars hit you while you're down, even better.
Hijacking- In this activity, you must first reach a target vehicle in a certain amount of time. Then you must get the vehicle to pull over by damaging it a certain amount, retrieve it, and bring it back to a garage. Damage the car by slamming and shooting it. Homies can really make a difference because members in the target vehicle will return fire. The cars you must retrieve will most likely belong to enemy gangs, so you will have gang members and cops on you as you attempt to drive it back. Be sure to use 'Rim Jobs' and 'Forgive and Forget' as needed.
Drug Trafficking- You must escort a dealer to various drug deals around Stilwater while being chased by gangs and police in this activity. The later levels can be very challenging. Recruit as many homies as you can since they will be a big help, but do not go out of your way to revive them. Just grab new ones when you can. Try to headshot the drivers of pursuing vehicles. This is the quickest way to dispose of them. Most importantly, be sure to switch cars as often as possible. As soon as you see light grey smoke, hop out.
Snatch- This activity requires you to recruit prostitutes and return them to a brothel. Before you can recruit a ho you must first kill their pimp. On some later levels you will have to rescue them from their pimp's car. Once again enemy gang members and cops will be in pursuit. Be sure to use a four door car so you can take the maximum number of prostitutes at a time. Also switch cars as soon as you can. Don't worry about homies, they will only limit the number of hos you can take.
Escort- This activity requires you to drive a car around, avoiding news vans, while a hooker pleases clients in the backseat. The news vans have a very large radius which is displayed as a red circle on your mini-map. Numerous vans will chase you so don't bother trying to shoot them. You must keep the client's pleasure bar up, and the media coverage bar low. On some levels you will have to evade the IRS and 'significant others.' You will also have to complete requests, like taking the client to a sex shop or hotel. The best way to avoid the news vans is by driving as fast as possible in the opposite lane of the highway. Hopefully the vans will crash into oncoming traffic.
Mayhem- Destruction is the only objective in this activity. You will be asked to go to an area of Stilwater and cause a certain amount of damage. The best part is you won't gain a wanted level for damage you do in the target area. The easiest way to do this is by restarting the level until you get an area with one of your cribs or a 'Rim Jobs.' In either case, retrieve one of your more expensive cars, such as an Attrazione. Destroy the vehicle any way you can. If the level will give you a bonus for using a certain weapon, use that. After you blow up your car quickly return to the marker and repair it for $500. Repeat this process until you reach the target amount of money. You can also drive through fences, lightpoles, and other small objects to build up large multipliers that will yield a great deal of money. In the final level, you can use all of Stilwater to cause destruction.
Altogether there are twenty-nine levels of activites that must be completed. Once you finish them all, the achievement will unlock.