At the moment, I'm considering the Pirates because they have the only name I know - Sidney Crosby.
Personally, if I didn't have a strong rooting interest in the Wings (being a life long Detroiter), I would probably throw my support behind Nashville. They are a pretty young team, and have never won. However, they have a lot of grit and two awesome defensemen (Ryan Suter and Shea Weber), who are fan favorites and do everything right. They have a lot to like, especially good coaching, defense and goaltending, all of which wins championships. They've been unsuccessful in the last, because they lacked good forwards, but they upgraded a lot this year. Anyway, if you want to try to choose the likeliest winner, I would probably say Vancouver or Pittsburgh, but if you want to root for a good squad I would go Nashville. But, if you want to root for beautiful hockey, then support the wings, who have the greatest artist currently playing.
I'm stuck between the Penguins, Red Wings, and the Predators. I love rooting for young teams (for example the Thunder in the NBA are my second favorite team), but since I'm in the position to bandwagon and pick a for sure good team, I'm inclined to pick the Wings.
I gotta run to work but we should meet up.