Best: Setting a scoring record that required you to take a photograph of the screen and mail it to the manufacturer only to find out that the photo didn’t come out well enough to actually see the score.
Worst: Being placed in charge of a Team Fortress clan, after only being with them a few weeks, and then having to assign players to their positions without knowing the skills of any of them. Had to make sure that every player got equal playing time which meant that all I was doing was watching matches and assigning times and positions without ever getting a chance to play myself. Ended up quitting after just a few more weeks of that hell.