I have used the cereal box problem many times over the years with my pre-service teachers. I never could explain adequately why the theoretical probability was around 14. It was never intuitive for them and they always estimated around 60. To show how long I have used it, my problem had stickers with the words MAY, THE, FORCE, BE WITH, YOU. My students have made me update the problem because they either laughed at me or reminded me that this was well before their time. (How did I get this old?)
The poke the hole problem I have had students do with a computer simulation. This is really the Monte Carlo method. I use it to find the area under a curve with non-calculus students (geometric probability). I make it more interesting by saying they are about to jump out of a plane. The beach is curved and the edge follows the function F(x) = sqrt(2) (or something like that). The waters are shark infested. Should you increase your insurance?