Shacks - Villa | You can car bomb, arson them, or do a drive by shooting. Car bomb uses a car. You need a gas can to arson. You need a gun with some clips and a car to do a drive by shooting.
You have a chance of going to the hospital with a car bomb.
Arson and drive by shooting has a chance of being caught and thrown in jail.
Penthouse - Castle | You can hire criminals to arson or bomb the properties. Cost will vary by property and there will be a higher chance of the criminals failing by how many guards have been hired.
Very slight chance of going to jail.
Private Island | You can hire criminals to shoot missiles or something onto the island or drop bombs from a plane. Cost will be expensive compared to the other properties.
Almost no chance of going to jail.
Chances of going to jail and the number of hours and happy loss can be determined by posts below or developers.