Easy "I'm Goin' In!" and "Softened 'Em Up" achievements
Rackets are part of the story. After a few missions, you will learn how to attack racket bosses and unlock their objectives on the map. To lure them out, you must complete certain objectives that are marked on the map. Each racket has two enforcers. They are marked by a skull icon on the map. For the "I'm Goin' In!" achievement, do not go to these skull icons when doing the racket objectives. Instead, you will have to do all the other objectives to cause enough havoc to the racket. Collect all the money at the objectives. Interrogate informants to find new objectives. Sometimes there are also vehicles driving around that belong to the racket -- destroying them also counts as damage. After causing enough damage, talk to your contact to get the "I'm Goin' In!" achievement (before going to the actual racket Boss fight). For the "Softened Em' Up" achievement, do the exact opposite and kill the two enforcers (marked by skull symbols on map). There are a lot of rackets in the game -- so you will have plenty of chances to get these achievements.