Let us imagine that we are brilliant, and came up with a way besides the classic Hockey League Simulator 2 to simulate 10,000 2009-10 seasons, from start to finish (in all of them, Marian Gaborik gets injured). Let us imagine these simulations are pretty darned accurate - the Gaborik injuries are a dead giveaway that they are.
Now we have a list of teams who've won the Stanley Cup in these 10,000 simulations - let us look at their average playoff wins. Someone like Detroit might have 9 or so, someone like the Islanders might have 0.1 or less. These numbers, however, are inherently meaningless when imagining who's going to win the Stanley Cup simply because some team has to win 16 games in the playoffs.
There's a lot of luck in the playoffs - it's rather improbable that despite the fact that Detroit and Pittsburgh were likely the two most talented teams in each of the last two seasons that both teams made it to the Stanley Cup Finals. When wondering about whether they'll repeat that feat, citing the above is not particularly important - it is certainly improbable, but still more probable than most Stanley Cup Finals pairings.