I'm a casual (Rangers) fan who definitely cannot argue or have that educated an opinion on who is more talented. But I feel hockey has a tremendous amount of luck involved, which probably evens out during the season, but makes the playoffs a complete crapshoot. (Billy Beane said about baseball playoffs, "My sh** doesn't work in the playoffs.")
Look at last night's rangers game for example. It was a tremendously close game. The Caps got lucky that the puck hit a defenders skate at a perfect angle a split second before the goalie's leg comes around, while the Rangers had more than a half dozen chances that could have just as easily been goals, but somehow missed the mark.
Last year the Kings beat the Rangers 4-1, implying they completely outclassed them. In reality, 3 of the 4 wins were in overtime, and each of those games could easily have gone the other way.
So yes, like most team sports, a playoff system means the best and most talented team will not always win. In soccer you'll have the winner of the league which is almost always, objectively, the best team. The winner of the FA Cup, on the other hand, is more often, objectively, not the best team.