Man Overbard is pretty much a "first film". It isn't a bad idea at all. And the talent, both in front of and behind the camera, is promising. But it needs direction. The script is an interesting first draft but needs some serious rewriting, especially continuity (there isn't much) and plot device set-ups, preferably by a proven script doctor. The actors all seem to be seasoned day players. There's often a reason why actors are day players. And here, that reason is apparent. (Maybe they were mostly all friends - that rarely works, either.) The director was mostly just stringing together scenes, not setting up the plot devices, the gags or the relationships.
Since this film was made 12-13 years ago, probably all the participants have gained more experience. Man Overboard was not a bad idea; in fact, it was a pretty good one. It would be interesting to see how it would have been improved. Perhaps they would be able to get back together for "Man Overboard II".