The four goals are to have everyone dislike you, slap 4 people, insult 5, and kick over all the trash cans. Some tips...
Everyone dislikes you : simply engage in conversation with people and insult them once. You should get a pop up window saying they don't like you anymore. Do this with everyone in town. Best to go to their houses in the evening, as most of them have jobs/go to the lake during the day.
Slap 4 people : In order to have the option to slap someone, they have to dislike you. Engage in conversation with someone (preferably at their house) and insult them. You should get a pop up saying they dislike you. Now pick the be rude option again and you should have the option to slap. Slap 4 people.
Insult 5 people : Same as slap, but you don't need to get them to dislike you first.
Kick over every trash can : It seems every house has a trash can, including yours. You might have to look around, some are out front, a couple are on the right side (from your perspective) and one or two were in the actual house. I wrote down the names of the people's houses as I did them so I knew who I did. Despite that, I still had to go back to a few houses and kick the cans again. Not sure why.