I got a chance to take this in a few times at the 2013 Twin Cities Film Fest (it ran multiple times as the lead-in to feature-length comedies).
Best words to describe the whole thing: clever, fun, light.
It could easily (at least in my opinion) be developed into a sitcom (for cable, network or subscription based service) or web series or could even be expanded into a feature film. But, having said that, it's really enjoyable as it is.
The story never drags, the dialogue and character interaction is believable and the cast is likable and easy to relate to (for the most part). When most shorts end, I don't really care what happens to the characters. Here though, I really want to see what becomes of everyone and how their collective story unfolds.
In terms of production quality, it was head and shoulders above most of the other entries I've seen at TCFF.
All of that added up to it winning Best Short Film - a much deserved honor.