Once you have unlocked the full map in game this trophy is obtainable. However I recommend either collecting 100 packages or using the cheat to unlock the Hunter helicopter and Rhino Tank. I personally prefer the tank. Once you have the tank it is invulnerable so just keep blowing stuff up and killing (You can be pulled out of the tank and busted or killed so keep moving). Once you have caused enough chaos especially against police/army you will break $1 mil in property damage. All damage including killing people and destroying cars counts (don't worry enemy tanks never shoot). Also this complements the Going green, Catch me if you can, and I'm famous achievements as well and is best done while going for those achievements.