Hypotheticals
I'm comparing the chances of winning in the O6 era to now, not the 30's. I understand and realize there was a salary cap then.
Parity of excellence? You do realize why teams had generally more stacked rosters 60 years ago vs today?
You fail to acknowledge the fact that the 40's, 50's and 60's Habs/Wings/Leafs would have NEVER:
1. Been able to stay constructed as they were with an NHL entry draft based on inverse order of NHL standings.
2. Been able to retain superstar talent en masse with a hard salary cap. In 1954 Chicago had TWO HOF players. The Bruins had THREE. The Habs had TEN. 10.
Also:
14 times from 43 and 67, the 1st seeded team won the SC.
That's better than half at 56%
2 times from 2006 to 2017, the 1st seeded team won the SC.
That's only 16.7%
You deal in hypotheticals while failing to acknowkedge realities.
The 1968 to 1992 era was defined by SC champions built thru the NHL Entry Draft or equivalent combined with the ability to exploit the inefficiencies of the other league teams.
Your hypotheticals fail to take into account economic realities. In real life the chances of a homeless person winning a lottery -Super Ball, Lotto Max, are identical to that of the richest person. Difference is in the ability to buy the lottery ticket. Spare change for a rich person, weeks food budget for a homeless person. Then you have the ability to manage and grow the winnings. So your numbers are nice but they fail to reflect hockey realities. Namely managing the team, draft picks, finding an appropriate coaching staff to develop the team and picks. These attributes define winning and are more complex then dividing 100 by 31 or the number of teams at any given time.
To appreciate the stranglehold Jim Norris Sr had on the 4 US O6 American teams, observe what happened soon after his death in 1952. Details of his interests in the 4 US teams below:
https://en.wikipedia.org/wiki/James_E._Norris
James D. Norris his son, VP of the Red Wings and part owner of the Hawks eventually left to takeover the Hawks. US anti-trust actions against the IBC - Norris boxing empire in the USA, extending somewhat beyond, eventually freed MSG - the Rangers and the Boston Garden - Bruins giving them autonomy.
Net result, without the NHL Entry Draft or equivalent by the 1960s,
Chicago had found the three best future NHL offensive players - Bobby Hull, Stan Mikita, Phil Esposito.
James D. Norris Jr:
https://en.wikipedia.org/wiki/James_D._Norris
New York with a larger scouting budget, signed Jean Ratelle and Rod Gilbert, while becoming the most successful team in the newly created NHL Amateur Draft(not a reverse order draft) in 1963, pre expansion selecting the likes of Brad Park, Tim Ecclestone, Syl Apps Jr, Joey Johnston, Don Luce.
Boston did well also - Bobby Orr, Bernie Parent, Derek Sanderson, signed.
The talent gap narrowed as the O6 era progressed, but the coaching and management gaps widened.
Point is that gap in management, coaching and development persisted. Post expansion the four non-Canadiens dynasties(two or more consecutive SC wins) were built thru the NHL Amateur/Entry Draft. NY Islanders(Bill Torrey), Edmonton Oilers(Glen Sather), Pittsburgh Penguins(Craig Patrick), Philadelphia Flyers(Keith Allen).
!991-92 saw a 22 team NHL, while 2016-17 featured 16 teams the difference between 22 and 30 teams is marginal, yet you have not had five dominating teams - adding the Canadiens to the above.
Major difference is that the last 37 or so seasons, NHL teams no longer develop their own coaches and management. Such hires are now made on the open market. Net result instead of a controlled transition from Frank Selke Sr to Sam Pollock, you have a throw out the old and bring in known outsiders approach which impacts stability and performance.