You just said that winning a Stanley Cup as a GM is overrated. That can easily be extrapolated to a coach, player, etc. You even imply that luck is more important. In the same breath you then put more importance on being competitive every year.
Do you listen to what you are saying?
I kind of get the point he's trying to make. If your competitive every year you have a shot at the cup every year. Luck, be it injuries to your or opponents key players, in game bounces, calls or non calls by the referees, that sort of thing does have to fall your way in order to win.
Conversely, we have the Oilers as an example. We went to the playoffs 12 years ago and came within a game of winning the Cup. Since then we missed the playoffs 10 years in a row, and 11 out of 12.
I would rather have a competitive, ie Playoff Team, every year as it gives us a chance. That said, in the years we squeaked into the playoffs every year and made 8th place, barely. We knew we couldn't compete and actually win a cup but making the playoffs was our "win". However that was in the pre cap era.
So now in the cap era, I would prefer to have a competitive team and a shot at winning the cup versus making it one year and the next not even come close. A good GM is judged by his teams overall competitiveness and consistency and Cup wins are the cherry on the cake.