Prize: Vacation trip to Mars; Trouble: They continue to be chased by the snow bear during the vacation on Mars.
Prize: A car/ship that converts into a bag for easy keeping; Trouble: The car/ship did it with Captain Good inside it.
Prize: Dinner at Ritz; Trouble: They dine at the kitchen and have to do the dishes.
Prize: Being painted by a famous artist; Trouble: They were literally painted.
Prize: A ride at a cruise boat; Trouble: They had to travel with the cargo.
Prize: A self massaging bed; Trouble: The bed beats them up with its robot hands.
Prize: Vacation time at a ski lodge; Trouble: They had to pull the sleigh.
Prize: A date with a computer-chosen partner; Trouble: He's got a date with the Wicked Witch of the West.
Prize: Vacation time at a dude ranch; Trouble: It's Fuddy's Dude Ranch. The first prize whose winners had a specific reason to dislike.
Prize: Roles in a movie made in Hollywood; Trouble: They had to make dangerous scenes.
Prize: Tickets to an Amusement Park named Funkyland; Trouble: They were the dunking clowns.
Prize: Tickets to the Rolling Clones; Trouble: They have to lay down at the floor with other viewers over them
Prize: Tickets for a flight on a luxury jet plane; Trouble: They didn't get seats inside the plane.